Insecticidal N&#39;-substituted-N,N&#39;-disubstitutedhydrazines

ABSTRACT

This invention relates to N&#39;-substituted-N,N&#39;-disubstitutedhydrazines of formula I ##STR1## wherein X and X&#39; are independently O, S, or NR; A&#39; and B&#39; are independently substituted or unsubstituted aryl or aromatic heterocycle; wherein F is alkyl, alkenyl, or aralkyl; and wherein E is a tertiary carbon containing organic radical having a total of at least four carbon and halogen atoms but not more than six halogen atoms, or a non-tertiary carbon containing non-haloalkyl organic or organometallic radical having at least five atoms other than hydrogen, oxygen and halogen which are useful as insecticides, compositions containing those compounds, methods of producing the compounds, and methods of their use. More particularly, the invention relates to insect growth regulating compounds and compositions, and methods of using such compounds and compositions. Compounds of the present invention are particularly suitable for controlling plant-destructive insects in crops of cultivated plants, ornamentals and forestry.

BACKGROUND OF THE INVENTION

This application is a continuation-in-part of pending application Ser. No. 300,871 filed Jun. 10, 1994, which is a continuation of abandoned application Ser. No. 688,357 filed Mar. 12, 1991, which is a continuation of abandoned application Ser. No. 384,079 filed Jul. 17, 1989, which is a continuation of abandoned application Ser. No. 911,177 filed Sep. 14, 1986, which is a continuation-in-part of application Ser. No. 789,797, filed Oct. 21, 1985, now U.S. Pat. No. 4,985,461; and a continuation-in-part of pending application Ser. No. 261,588 filed Jun. 17, 1994, which is a division of pending application Ser. No. 843,487 filed Feb. 28, 1992, which is a division of application Ser. No. 715,843, filed Jun. 14, 1991, now U.S. Pat. No. 5,117,057, which is a continuation of abandoned application Ser. No. 091,687 filed Aug. 31, 1987, which is a continuation-in-part of abandoned application Ser. No. 024,660 filed Mar. 11, 1987, which is a continuation-in-part of abandoned application Ser. No. 821,187 filed Jan. 22, 1986, and a continuation-in-part of abandoned application Ser. No. 858,482 filed May 1, 1986, and a continuation-in-part of abandoned application Ser. No. 911,177, filed Sep. 14, 1986, and a continuation-in-part of abandoned application Ser. No. 911,928 filed Sep. 26, 1986, and a continuation-in-part of abandoned application Ser. No. 012,380 filed Feb. 19, 1987, which is a continuation-in-part of abandoned application Ser. No. 885,508 filed Jul. 14, 1986, and a continuation-in-part of abandoned application Ser. No. 005,824 filed Feb. 4, 1987, which is a continuation-in-part of abandoned application Ser. No. 835,073 filed Feb. 28, 1986; and a continuation-in-part of pending application Ser. No. 843,487; and continuation-in-part of pending application Ser. No. 129,549 filed Sep. 24, 1993, now U.S. Pat. No. 5,530,028, which is a continuation-in-part of application Ser. No. 984,189, filed Nov. 23, 1992, now U.S. Pat. No. 5,344,958.

This invention relates to N'-substituted-N,N'-disubstitutedhydrazines, which are useful as insecticides, compositions containing those compounds and methods of their use. More particularly, the invention relates to insect growth regulating compositions, and methods of using such compositions. Compounds of the present invention are particularly suitable for controlling plant-destructive insects in crops of cultivated plants, ornamentals and forestry.

The search for compounds which have a combination of excellent insecticidal activity and low undesirable toxicity is a continuing one because of factors such as the desire for compounds exhibiting greater activity, better selectivity, low undesirable environmental impact, low production cost and effectiveness against insects resistant to many known insecticides.

Certain hydrazine derivatives have been disclosed in the literature. However, none of the prior art literature suggests hydrazines derivatives having insect growth regulating characteristics.

U.S. Pat. No. 3,481,972 discloses 2-(beta-hydroxyethyl)-2-methyl acid hydrazine compounds of the formula ZC(O)NHN(CH₃)CH₂ CH₂ OH where Z represents furyl, cyclohexyl, phenyl, benzyl, styryl, dihydrostyryl or substituted phenyl. The compounds are stated to be useful as pesticides for the control of such organisms as insects, arachnids, nematodes, fungi, plants and helminth organisms.

U.S. Pat. No. 4,062,934 discloses compounds of the formula ##STR2## where R₃ and R₄ represent a hydrogen atom or a one to four alkyl and n is an integer from zero to four. These compounds are used as X-ray contrast media.

U.S. Pat. No. 4,189,482 discloses compounds of the formula ##STR3## where R₃ is lower alkyl, or substituted or unsubstituted phenyl, benzyl, phenethyl, thienyl or furyl; R₄ is hydrogen or lower alkyl; and X is --N₃, --CH₂ --CH₂ --OH, --CH₂ CH₂ -halide and --CH₂ CH₂ OSO₂ CH₃ as intermediates to penicillins having an imino substituted piperazindioncarbonylamino aceyl side chains.

U.S. Pat. No. 4,317,741 discloses a poly(oxyalkylated)hydrazine of the formula ##STR4## where R is hydrogen, (C₁ -C₄)alkyl, phenyl or mixtures thereof and the sum of w, x, y and z is from about four to about 20. These compounds are used as corrosion inhibitors.

U.S. Pat. No. 4,357,351 discloses five specific compounds (Compound Nos. 400 and 402-404) of the formula ##STR5## where n averages 7.7 and n' averages 11. These compounds are disclosed to have leptericidal activity. However, they are not claimed and it is not seen how these five compounds are included in the generic formula disclosed in the patent.

U.S. Pat. No. 4,547,524 discloses a class of benzoyl hydrazone derivatives which have insecticidal activity. However, the unsaturated carbon is bonded to hydrogen, lower alkyl, or phenyl, or forms part of a cyclohexane ring. Further the N'-substituent is not taught to include a tertiary carbon atom.

U.S. Pat. No. 4,564,611 discloses (di)thiophosphoric and -phosphonic acid derivatives having the formula ##STR6## in which R denotes (C₁ -C₄)-alkyl; R₁ denotes (C₁ -C₄)-alkyl, (C₁ -C₄)-alkoxy, (C₁ -C₄)-alkylmercapto, (C₁ -C₄)-alkylamino or di(C₁ -C₄)alkylamino; R₂ and R₃ independently of one another denote hydrogen, (C₁ -C₄)-alkyl, (C₅ -C₆)-cycloalkyl, benzyl or furylmethyl; R₄ denotes (C₁ -C₄)-alkyl, (C₁ -C₃)-alkoxymethyl, (C₁ -C₃)-alkylmercaptomethyl or phenyl and X denotes oxygen or sulfur, which have activity against sucking and biting insects, acarides and nematodes, and display good fungicidal activity. Insect growth regulating activity is not disclosed. Further, R₂ is not taught to include a tertiary carbon.

The Chemical Abstracts citation CA 84(21):150168j indicates that Azerb Khim Zh, 1975, (5), 47-8 discloses Me₂ CHCH₂ CH═NN(Ac)CH₂ CH₂ OH, PhCH═NN(Ac)CH₂ CH₂ OH and Me₂ CHCH═NN(Ac)CH₂ CH₂ OH which have pesticidal activity.

In 88 J.A.C.S, 4677-4681 (1966) N'-t-butyl-N'-methylcarbonyl-N-benzoylhydrazine is disclosed. No biological activity is disclosed.

In 37 Tetrahedron Letters, 3575-3578 (1979), the result of an electron spin resonance study is reported. The hydrazyl radicals produced included PhC(O)N(t-Bu)NC(O)Ph and PhC(O)N(Et₃ Si)NC(O)Ph. No utility was suggested for the radicals which were studied.

In 25 Aust. J. Chem, 523-529 (1972), several N,N'-dibenzoylhydrazine derivatives are disclosed including N'-i-propyl-; N'-n-propyl-; N'-(2-methylpropyl)-; N'-(3-methylbutyl)-; N'-benzyl- and N'-phenyl-N,N'-dibenzoylhydrazine in which one or both nitrogen atoms are alkylated or phenylated. No biological activity is disclosed for those compounds.

In 61 Helv. Chim. Acta, 1477-1510 (1978), several N,N'-dibenzoylhydrazine and hydrazide derivatives including N'-t-butyl-N-benzoyl-N'-(4-nitrobenzoyl)-hydrazine are disclosed. No biological activity is disclosed for those compounds.

In 44 J.A.C.S., 2556-2567 (1922), isopropylhydrazine (CH₃)₂ CH--NH--NH₂, symmetrical diisopropylhydrazine, dibenzoylisopropylhydrazine and certain derivatives are disclosed. No biological activity is disclosed for those compounds.

In 44 J.A.C.S., 1557-1564 (1972), isopropyl, methyl and bornyl semicarbazides are disclosed. No biological activity is disclosed for those compounds.

In 48 J.A.C.S., 1030-1035 (1926), symmetrical di-methylphenylmethylhydrazine and certain related compounds including 1,2-bis-methylphenylmethyl-4-phenyl-semicarbazide are disclosed. No biological activity is disclosed for those compounds.

In 27 Bull. Chem. Soc. Japan, 624-627 (1954), certain hydrazine derivatives including alpha,beta-dibenzoylphenylhydrazine are disclosed. No biological activity is disclosed for those compounds.

In J. Chem. Soc. (C), 1531-1536 (1966), N,N'-dibenzoylphenylhydrazine and N-acetyl-N'-benzoyl-p-nitrophenylhydrazine are disclosed. No biological activity is disclosed for those compounds.

In 56B Chem. Berichte, 954-962 (1923), symmetrical di-isopropylhydrazines, symmetrical diisobutyl- and certain derivatives including N,N'-diisobutyldibenzoyl-hydrazine are disclosed. No biological activity is disclosed for those compounds.

In 590 Annalen der Chemie, 1-36 (1954), certain N,N'-dibenzoylhydrazine derivatives are disclosed including N'-methyl- and N'-(2-phenyl)-isopropyl-N,N'-dibenzoylhydrazine. No biological activity is disclosed for those compounds.

In J. Chem. Soc. 4191-4198 (1952), N,N'-di-n-propylhydrazine, N,N'-dibenzoylhydrazine and bis-3,5-dinitrobenzoyl are disclosed. No biological activity is disclosed for those compounds.

In 32 Zhur. Obs. Khim., 2806-2809 (1962), N'-2,4-methyl-2,4-pentadiene-N,N'-dibenzoylhydrazine is disclosed. No biological activity is disclosed.

In 17 Acta. Chim. Scand., 95-102 (1963), 2-benzoylthiobenzoylhydrazide (C₆ H₅ --CS--NHNH--CO--C₆ H₅) and certain hydrazone and hydrazine derivatives are disclosed including 1,2-dibenzoyl-benzylhydrazine. No biological activity is disclosed for those compounds.

In 25 Zhur. Obs. Khim, 1719-1723 (1955), N,N'-bis-cyclohexylhydrazine and N,N'-dibenzoylcyclohexylhydrazine are disclosed. No biological activity is disclosed for those compounds.

In J. Chem. Soc., 4793-4800 (1964), certain dibenzoylhydrazine derivatives are disclosed including tribenzoylhydrazine and N,N'-dibenzoylcyclohexylhydrazine. No biological activity is disclosed for those compounds.

In 36 J. Prakt. Chem., 197-201 (1967), certain dibenzoylhydrazine derivatives including N'-ethyl-; N'-n-propyl-; N'-isobutyl-; N'-neopentyl-; N'-n-heptyl-; and N'-cyclohexylmethyl-N,N'-dibenzoylhydrazines are disclosed. No biological activity is disclosed for those compounds.

In 26 J.O.C., 4336-4340 (1961) N'-t-butyl-N,N'-di-(t-butoxycarbonyl)hydrazide is disclosed. No biological activity is disclosed.

In 41 J.O.C., 3763-3765 (1976), N'-t-butyl-N-(phenylmethoxycarbonyl)-N'-(chlorocarbonyl)hydrazide is disclosed. No biological activity is disclosed.

In 94 J.A.C.S., 7406-7416 (1972) N'-t-butyl-N,N'-dimethoxycarbonylhydrazide is disclosed. No biological activity is disclosed.

In 43 J.O.C., 808-815 (1978), N'-t-butyl-N-ethoxycarbonyl-N'-phenylaminocarbonylhydrazide and N'-t-butyl-N-ethoxycarbonyl-N'-methylaminocarbonylhydrazide are disclosed. No biological activity is disclosed for those compounds.

In 39 J. Econ. Ent., 416-417 (1946), certain N-phenyl-N'-acylhydrazines are disclosed and evaluated for their toxicity against codling moth larvae.

Compounds of the present invention are distinguished by their excellent insecticidal activity, particularly against insects of the orders Lepidoptera and Coleoptera, and most particularly by their insect growth regulating activity without material adverse impact on beneficial insects.

DETAILED DESCRIPTION OF THE INVENTION

This invention relates to compounds having the nucleus of the formula ##STR7## wherein N is nitrogen; where X and X' are independently O, S, or NR, with R as defined below; wherein A' and B' are independently substituted or unsubstituted aryl or aromatic heterocycle; wherein F is hydrogen, alkyl, alkenyl, or aralkyl; wherein E is a tertiary carbon containing organic radical, a haloalkyl having a total of at least four carbon and halogen atoms but not more than six halogen atoms, or a non-tertiary carbon containing non-haloalkyl organic or organometallic radical having at least five atoms other than hydrogen, oxygen and halogen; provided that E is not a straight chain alkyl, --CH₂ CH₂ N(CH₂ CH₃)₂, cyclohexyl, a six-membered cyclic containing organic radical, a cyclic aromatic radical, or an organic radical containing ##STR8## provided that E is not a sulfur or oxygen containing organic radical; provided that E does not have a chain length of non-hydrogen atoms greater than five; provided that when A' and B' are phenyl and F is hydrogen, then E is not neopentyl; provided that when A' is phenyl, F is hydrogen, and E is t-butyl, then B' is not 4-nitrophenyl; where organic radical is a radical comprising at least one carbon atom, but no metal atoms; and where organometallic radical is a radical containing a carbon-to-metal bond; or an agronomically acceptable salt thereof.

The invention also relates to a method of regulating insect growth which comprises contacting insects with a compound having the nucleus of Formula I, or an agronomically acceptable salt thereof.

Compounds of this invention with good insecticidal activity include those of Formula II: ##STR9## wherein X and X' are independently selected from O, S and NR, wherein R is selected from hydrogen and (C₁ -C₆)alkyl;

E is selected from;

1. an unsubstituted tertiary-carbon containing (C₄ -C₁₀) alkyl wherein the substituents are independently selected from 1 to 4 alkenyl, cyano, cycloalkyl, halogen, and phenyl and wherein the sum of non-hydrogen atoms in E is from 4 to 14, E does not have a chain length of non-hydrogen atoms greater than 5, and E does not contain more than one cyano group; and

2. an unsubstituted or substituted non-tertiary-carbon containing (C₄ -C₁₀) alkyl wherein the substituents are independently selected from 1 to 4 alkenyl, cyano, cycloalkyl, halogen, phenyl, and trimethylsilyl and wherein the sum of non-hydrogen atoms in E is from 5 to 14, E does not have a chain length of non-hydrogen atoms greater than 5, and E does not contain more than one cyano group;

A and B are independently selected from;

1. unsubstituted or substituted naphthyl wherein the substituents are independently selected from 1 to 3 halo; nitro; (C₁ -C₄)alkoxy; (C₁ -C₄)alkyl; and amino;

2. unsubstituted or substituted phenyl wherein the substituents are independently selected from 1 to 5 halo; nitro; cyano; hydroxy; (C₁ -C₆)alkyl; (C₁ -C₆)haloalkyl; (C₁ -C₆)cyanoalkyl; (C₁ -C₆)hydroxyalkyl; (C₁ -C₆)alkoxy; (C₁ -C₆)haloalkoxy; (C₁ -C₆)alkoxy(C₁ -C₆)alkyl; (C₁ -C₆)alkoxy(C₁ -C₆)alkoxy; (C₁ -C₆)alkylthio(C₁ -C₆)alkoxy; (C₁ -C₆)alkanoyloxy(C₁ -C₆)alkyl; (C₂ -C₆)alkenyl optionally substituted with halo, cyano, (C₁ -C₄)alkyl, or (C₁ -C₄)alkoxy; (C₂ -C₆)alkenyloxy; (C₂ -C₆)alkenylcarbonyl; (C₂ -C₆)alkenyloxycarbonyloxy; (C₂ -C₆)alkynyl optionally substituted with halo or (C₁ -C₄)alkyl; carboxy; (C₁ -C₆)alkylcarboxy(C₁ -C₆)alkyl); (C₁ -C₆)alkylcarbonyl; (C₁ -C₆)haloalkylcarbonyl; (C₁ -C₆)alkoxycarbonyl; (C₁ -C₆)haloalkoxycarbonyl; (C₁ -C₆)alkanoyloxy (--OCOR); (C₁ -C₆)alkoxycarbonyl(C₁ -C₆)alkoxy; amino (--NRR'); carboxamido (--CONRR'); (C₂ -C₆)alkenylcarbonylamino; (C₁ -C₆)hydroxyalkylaminocarbonyl; aminocarbonyloxy (--OCONRR'); amido (--NRCOR'); alkoxycarbonylamino (--NRCO₂ R'); thiocyanato; isothiocyanato; (C₁ -C₆)thiocyanatoalkyl; (C₁ -C₆)alkylthio; sulfoxide (--S(O)R); sulfonyl (--SO₂ R); alkylsulfonyloxy (--OSO₂ R); sulfonamide (--SO₂ NRR'); alkylthiocarbonyl (--CSR); thioamido (--NRCSR'); unsubstituted or substituted phenyl wherein the substituents are independently selected from 1 to 3 halo, cyano, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)haloalkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino, and (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; unsubstituted or substituted phenoxy wherein the substituents are independently selected from 1 to 3 halo, cyano, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)haloalkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino, and (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; unsubstituted or substituted benzoyl wherein the substituents are independently selected from 1 to 3 halo, cyano, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)haloalkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino and (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; benzoyloxy(C₁ -C₆)alkyl; phenylthio(C₁ -C₆)alkyl wherein the phenyl ring is unsubstituted or substituted with 1 to 3 substituents independently selected from halo, cyano, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)haloalkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino, and (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; imino (--CR═N--R²) wherein R² is selected from hydroxy, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, amino (--NRR'), phenylamino, carbonyl (--COR), and benzoyl; acetylthiosemicarbazone; or when two adjacent positions on the phenyl ring are substituted with alkoxy groups, these groups, together with the carbon atoms to which they are attached, may be joined to form a 5 or 6 membered dioxolano or dioxano heterocyclic ring; and

3. unsubstituted or substituted five-membered heterocycle selected from furyl, thienyl, triazolyl, pyrrolyl, isopyrrolyl, pyrazolyl, isoimidazolyl, thiazolyl, isothiazolyl, oxazolyl, and isooxazolyl wherein the substituents are independently selected from 1 to 3 halo; nitro; hydroxy; (C₁ -C₆)alkyl; (C₁ -C₆)alkoxy; carboxy; (C₁ -C₆)alkoxycarbonyl (--CO₂ R); (C₁ -C₆)alkylcarboxy(C₁ -C₆)alkyl (--RCO₂ R'); carboxamido (--CONRR'); amino (--NRR'); amido (--NRCOR'); (C₁ -C₆)alkylthio; or unsubstituted or substituted phenyl wherein the substituents are independently selected from one to three halo, nitro, (C₁ -C₆)alkyl, (C₁ -C₆)haloalkyl; (C₁ -C₆)alkoxy; (C₁ -C₆)haloalkoxy; carboxy, (C₁ -C₄)alkoxycarbonyl (--CO₂ R); or amino (--NRR');

wherein R, R' and R" are selected from hydrogen and (C₁ -C₆)alkyl;

and agronomically acceptable salts thereof;

provided that

when X and X' are O and A and B are unsubstituted phenyl, then E is other than isopropyl (--CH(CH₃)₂); 2-methylpropyl (--CH₂ CH(CH₃)₂); 3-methylbutyl (--CH₂ CH₂ CH(CH₃)₂); neopentyl (2,2-dimethylpropyl; --CH₂ C(CH₃)₃) or cyclohexylmethyl (--CH₂ C₆ H₁₁); or

when X and X' are O, A is unsubstituted phenyl or phenyl substituted with 1 to 2 substituents independently selected from (C₁ -C₆)alkyl, and B is unsubstituted phenyl or phenyl substituted with 1 to 2 substituents independently selected from halo, nitro, and (C₁ -C₆)alkyl, then E is other than halo(C₂ -C₆)alkyl; or

when X and X' are O, E is t-butyl (--C(CH₃)₃), and A is unsubstituted phenyl, then B is other than 4-nitrophenyl; and

when one of A and B is an unsubstituted or substituted five-membered heterocycle the other of A and B is other than an unsubstituted or substituted five-membered heterocycle.

Because of their enhanced insecticidal activity, preferred compounds are those of Formula II wherein X and X' are independently selected from O and S; E is selected from (1) an unsubstituted or substituted tertiary-carbon containing (C₃ -C₁₀) alkyl wherein the substituents are independently selected from 1 to 4 alkenyl, cyano, cycloalkyl, halogen, and phenyl and wherein the sum of non-hydrogen atoms in E is from 4 to 14, E does not have a chain length of non-hydrogen atoms greater than 5, and E does not contain more than one cyano group; (2) an unsubstituted or substituted non-tertiary-carbon containing (C₄ -C₁₀) alkyl wherein the substituents are independently selected from 1 to 4 alkenyl, cyano, cycloalkyl, halogen, phenyl, and trimethylsilyl and wherein the sum of non-hydrogen atoms in E is from 5 to 14; and A and B are independently selected from (1) unsubstituted or substituted naphthyl wherein the substituents are independently selected from 1 to 3 halo; nitro; (C₁ -C₄)alkoxy; (C₁ -C₄)alkyl; and amino; (2) unsubstituted or substituted phenyl wherein the substituents are independently selected from 1 to 5 halo; nitro; cyano; hydroxy; (C₁ -C₆)alkyl; (C₁ -C₆)haloalkyl; (C₁ -C₆)cyanoalkyl; (C₁ -C₆)hydroxyalkyl; (C₁ -C₆)alkoxy; (C₁ -C₆)haloalkoxy; (C₁ -C₆)alkoxy(C₁ -C₆)alkyl; (C₁ -C₆)alkoxy(C₁ -C₆)alkoxy; (C₁ -C₆)alkylthio(C₁ -C₆)alkoxy; (C₁ -C₆)alkanoyloxy(C₁ -C₆)alkyl; (C₂ -C₆)alkenyl optionally substituted with halo, cyano, (C₁ -C₄)alkyl, or (C₁ -C₄)alkoxy; (C₂ -C₆)alkenyloxy; (C₂ -C₆)alkenylcarbonyl; (C₂ -C₆)alkenyloxycarbonyloxy; (C₂ -C₆)alkynyl optionally substituted with halo or (C₁ -C₄)alkyl; carboxy; (C₁ -C₆)alkylcarboxy(C₁ -C₆)alkyl); (C₁ -C₆)alkylcarbonyl; (C₁ -C₆)haloalkylcarbonyl; (C₁ -C₆)alkoxycarbonyl; (C₁ -C₆)haloalkoxycarbonyl; (C₁ -C₆)alkanoyloxy (--OCOR); (C₁ -C₆)alkoxycarbonyl(C₁ -C₆)alkoxy; amino (--NRR'); carboxamido (--CONRR'); (C₂ -C₆)alkenylcarbonylamino; (C₁ -C₆)hydroxyalkylaminocarbonyl; aminocarbonyloxy (--OCONRR'); amido (--NRCOR'); alkoxycarbonylamino (--NRCO₂ R'); thiocyanato; isothiocyanato; (C₁ -C₆)thiocyanatoalkyl; (C₁ -C₆)alkylthio; sulfoxide (--S(O)R); sulfonyl (--SO₂ R); alkylsulfonyloxy (--OSO₂ R); sulfonamide (--SO₂ NRR'); alkylthiocarbonyl (--CSR); thioamido (--NRCSR'); unsubstituted or substituted phenyl wherein the substituents are independently selected from 1 to 3 halo, cyano, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)haloalkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino, and (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; unsubstituted or substituted phenoxy wherein the substituents are independently selected from 1 to 3 halo, cyano, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)haloalkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino, and (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; unsubstituted or substituted benzoyl wherein the substituents are independently selected from 1 to 3 halo, cyano, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)haloalkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino and (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; benzoyloxy(C₁ -C₆)alkyl; phenylthio(C₁ -C₆)alkyl wherein the phenyl ring is unsubstituted or substituted with 1 to 3 substituents independently selected from halo, cyano, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)haloalkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino, and (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; imino (--CR═N--R²) wherein R² is selected from hydroxy, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, amino (--NRR'), phenylamino, carbonyl (--COR), and benzoyl; acetylthiosemicarbazone; or when two adjacent positions on the phenyl ring are substituted with alkoxy groups, these groups, together with the carbon atoms to which they are attached, may be joined to form a 5 or 6 membered dioxolano or dioxano heterocyclic ring; and agronomically acceptable salts thereof.

Because of their excellent insecticidal activity, more preferred compounds are those of Formula II wherein X and X' are O or S; F is branched (C₃ -C₈)alkyl; A and B are the same or different unsubstituted naphthyl or unsubstituted or substituted phenyl wherein the substituents are independently selected from 1 to 5 halo; nitro; cyano; lower (C₁ -C₄)alkyl; lower (C₁ -C₄)haloalkyl; lower (C₁ -C₄)cyanoalkyl; lower (C₁ -C₄)alkoxy; lower (C₁ -C₄)alkoxyalkyl having independently the stated number of carbon atoms in each alkyl group; carbonyl (--COR); lower (C₁ -C₄)alkoxycarbonyl; lower (C₁ -C₄)alkanoyloxy; thiocyanato; unsubstituted or substituted phenyl having one or two of the same or different halo, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino or (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; or phenoxy where the phenyl ring is unsubstituted or substituted with one or two of the same or different halo, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino or (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group where R is hydrogen or (C₁ -C₄)alkyl; and agronomically acceptable salts thereof.

Because of their outstanding insecticidal activity, even more preferred compounds are those of Formula II wherein X and X' are O; E is branched (C₄ -C₇)alkyl; A and B are independently selected from unsubstituted or substituted phenyl wherein the substituents are independently selected from 1 to 3 halo, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, or (C₁ -C₄)haloalkyl; and agronomically acceptable salts thereof. Most preferred are those compounds of Formula II wherein X and X' are O, E is selected from tertiary butyl, neopentyl (2,2-dimethylpropyl), and 1,2,2-trimethylpropyl; A and B are independently selected from unsubstituted phenyl or substituted phenyl wherein the substituents are independently selected from 1 to 3 chloro, fluoro, bromo, iodo, nitro, methyl, ethyl, methoxy, trifluoromethoxy, and trifluoromethyl; and agronomically acceptable salts thereof.

The pattern of substitution on A and B, when A and B are substituted phenyl, affects the insecticidal activity. The preferred pattern are represented by Formula III: ##STR10## The more preferred substituent patterns for the left-side phenyl group of Formula III is wherein R^(a) and R^(b) are other than hydrogen and R^(h) is hydrogen or wherein R^(h) is other than hydrogen and R^(a) and R^(b) are hydrogen. The more preferred substituent pattern for the right-side phenyl group of Formula III is wherein R^(c) and R^(e) are hydrogen and wherein R^(d) and R^(f) are other than hydrogen. Preferred compounds of Formula III are wherein R^(a) is selected from hydrogen, halo and (C₁ -C₆)alkyl; R^(b) is selected from hydrogen and unsubstituted or halo (preferrably fluoro) substituted (C₁ -C₆)alkoxy; R^(c) is selected from hydrogen, halo, (C₁ -C₆)alkyl, (C₁ -C₆)alkoxy, (C₁ -C₆)alkoxy(C₁ -C₆)alkyl, and nitro; R^(d), R^(e) and R^(f) are each independently selected from hydrogen, bromo, chloro, fluoro, (C₁ -C₆)alkyl, (C₁ -C₆)alkoxy, and (C₁ -C₆)alkoxy(C₁ -C₆)alkyl; R^(g) is a branched (C₄ -C₆)alkyl; R^(h) is selected from hydrogen, (C₁ -C₆)alkoxy, (C₁ -C₆)alkyl, or when taken together with R^(b) is methylenedioxy (--OCH₂ O--), 1,2-ethylenedioxy (--OCH₂ CH₂ O--), 1,2-ethyleneoxy (--CH₂ CH₂ O--) or 1,3-propyleneoxy (--CH₂ CH₂ CH₂ O--) wherein an oxo atom is located at the R^(b) position; and the substituent pairs selected from R^(c) and R^(d), and R^(d) and R^(e), and R^(e) and R^(f) when taken together can be methylenedioxy or 1,2-ethylenedioxy; provided that one of R^(a) and R^(b) and R^(h) must be other than hydrogen and that one of R^(c) and R^(d) and R^(e) and R^(f) must be other than hydrogen; and agronomically acceptable salts thereof.

The term "halo" should be understood as including chloro, fluoro, bromo and iodo. The term "alkyl" by itself or as a part of another substituent, unless otherwise stated, includes straight or branched chain groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, isobutyl, neopentyl and the like and, where indicated, higher homologues and isomers such as n-octyl, isooctyl and the like. The term "haloalkyl" by itself or as part of another substituent is an alkyl group of the stated number of carbon atoms having one or more halo atoms bonded thereto such as chloromethyl, 1- or 2-bromoethyl, trifluoromethyl and the like. Analogously, "cyanoalkyl" by itself or as part of another group is an alkyl group of the stated number of carbon atoms having one or more cyano groups bonded thereto; "haloalkoxy" by itself or as part of another group is an alkoxy group of the stated number of carbon atoms having one or more halo atoms bonded thereto such as difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2,2,2-trifluoroethoxy and the like. "Alkenyl" and "alkynyl" by themselves or as part of another substituent comprise straight and branched chain groups of the stated number of carbon atoms. "Alkadienyl" is a straight or branched chain alkenyl group comprising two carbon-to-carbon double bonds that can be conjugated such as 1,3-butadienyl, cumulated such as 1,2-propadienyl or isolated such as 1,4-pentadienyl.

The term "organic radical" should be understood to mean a radical comprising at least one carbon atom but no metal atoms. Examples of organic radicals include alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heterocycles, esters, ethers, thio derivatives and amine derivatives.

The term "organometallic radical" should be understood to include radicals containing a carbon-to-metal bond. Examples of such radicals include trimethylsilyl.

The term "tertiary carbon" is meant to refer to a carbon having at least three carbon-to-carbon single bonds.

The term "aryl" should be understood to include those molecules which have a ring structure characteristic of benzene, naphthalene, phenanthrene and anthracene, that is either the six-carbon ring of benzene or the condensed six-carbon rings of other aromatic derivatives. Examples of aryl radicals include unsubstituted and substituted phenyl, benzyl and naphthalene.

The term "cyclic aromatic radical" should be understood to mean unsaturated cyclic compounds including heterocyclic compounds. Examples of cyclic aromatic radicals include aryl, indolyl, thienyl, furyl, pyrrolyl, triazolyl and tetrazolyl.

Representative examples of six-membered heterocycles having one, two, three or four nitrogen atoms and two to five nuclear carbon atoms include 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, 5-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 3-pyrazinyl, 2-(1,3,5-triazinyl), 3-(1,2,4-triazinyl), 5-(1,2,4-triazinyl), 6-(1,2,4-triazinyl), 4-(1,2,3-triazinyl) and 5-(1,2,3-triazinyl).

Representative examples of five-membered heterocycles include 2-furyl; 3-furyl; 2-thienyl; 3-thienyl; 4-(1,2,3-triazolyl); 3-(1,2,4-triazolyl); 5-(1,2,4-triazolyl), 2-pyrrolyl; 2-oxazolyl; and the like.

Those N'-substituted-N,N'-diacylhydrazines of Formula I which possess acidic or basic functional groups may be further reacted to form novel salts with appropriate bases or acids. These salts also exhibit pesticidal activity. Typical salts are the agronomically acceptable metal salts, ammonium salts and acid addition salts. Among the metal salts are those in which the metal cation is an alkali metal cation such as sodium, potassium, lithium or the like; alkaline earth metal cation such as calcium, magnesium, barium, strontium or the like; or heavy metal cation such as zinc, manganese, cupric, cuprous, ferric, ferrous, titanium, aluminum or the like. The ammonium salts include those in which the ammonium cation has the formula NR⁵ R⁶ R⁷ R⁸ wherein each of R⁵, R⁶, R⁷ and R⁸ are independently hydrogen, hydroxy, (C₁ -C₄)alkoxy, (C₁ -C₂₀)alkyl, (C₃ -C₈)alkenyl, (C₃ -C₈)alkynyl, (C₂ -C₈)hydroxyalkyl, (C₂ -C₈)alkoxyalkyl, (C₂ -C₆)aminoalkyl, (C₂ -C₆)haloalkyl, amino, (C₁ -C₄)alkyl- or (C₁ -C₄)dialkylamino, substituted or unsubstituted phenyl, substituted or unsubstituted phenylalkyl, having up to four carbon atoms in the alkyl moiety, or any two of R⁵, R⁶, R⁷ or R⁸ can be taken together to form with the nitrogen atom a 5- or 6-membered heterocyclic ring, optionally having up to one additional hetero atom (e.g., oxygen, nitrogen, or sulfur) in the ring, and preferably saturated, such as piperidino, morpholino, pyrrolidino, piperazino or the like, or any three of R⁵, R⁶, R⁷ or R⁸ can be taken together to form with the nitrogen atom a 5- or 6-membered aromatic heterocyclic ring, such as piperazole or pyridine. When R⁵, R⁶, R⁷ or R⁸ substituent in the ammonium group is a substituted phenyl or substituted phenylalkyl, the substituents on the phenyl and phenylalkyl will generally be selected from halo, (C₁ -C₈)alkyl, (C₁ -C₄)alkoxy, hydroxy, nitro, trifluoromethyl, cyano, amino, (C₁ -C₄)alkylthio and the like. Such substituted phenyl groups preferably have up to two such substituents. Representative ammonium cations include ammonium, dimethylammonium, 2-ethylhexylammonium, bis(2-hydroxyethyl)ammonium, tris(2-hydroxyethyl)ammonium, dicyclohexylammonium, t-octylammonium, 2-hydroxyethylammonium, morpholinium, piperidinium, 2-phenethylammonium, 2-methylbenzylammonium, n-hexylammonium, triethylammonium, trimethylammonium, tri(n-butyl)-ammonium, methoxyethylammonium, diisopropylammonium, pyridinium, dialkylammonium, pyrazolium, propargylammonium, dimethylhydrazinium, octadecylammonium, 4-dichlorophenylammonium, 4-nitrobenzylammonium, benzyltrimethylammonium, 2-hydroxy-ethyldimethyloctadecylammonium, 2-hydroxyethyldiethyloctylammonium, decyltrimethylammonium, hexyltriethylammonium, 4-methylbenzyltrimethylammonium, and the like. Among the acid addition salts are those in which the anion is an agronomically acceptable anion such as hydrochloride, hydrobromide, sulfate, nitrate, perchlorate, acetate, oxalate and the like.

For insects to successfully grow, that is progress from one larval stage to the next larger larval stage or metamorphose to an adult stage, they must moult or shed the old cuticle. Compounds of this invention are insect growth regulators in that they interfere with this natural moulting and other growth-regulated processes.

Growth regulatory effects are not usually expressed rapidly after treatment. This is contrary to conventional insecticides, such as neurotoxins, respiratory poisons and the like, which affect vital processes and which are noted for rapidity of effect.

For example, compounds such as:

    (R.sup.1).sub.2 --P(X)X(CH.sub.2).sub.n C(O)NHN(R")C(O)C.sub.5 H.sub.6,

where R¹ =lower alkyl, alkoxy, thioalkyl and may be identical or different, X=O or S, n=0-5, and R"=t-butyl would constitute conventional, fast-acting, cholinesterase-inhibiting neurotoxins with efficacy anticipated against a comparatively broad range of insect orders and acarides as well as non-target organisms such as mammals, fish and birds. By contrast insect growth regulators as claimed herein would be somewhat less rapid in effect with activity being confined to particular insects which are largely pestiferous and including those strains resistant to organophosphate insecticides. Although somewhat slower to act than conventional cholinesterese-inhibiting neurotoxins, compounds of this invention are sufficiently rapid-acting so as to protect agricultural crops and are therefore superior to other known insect growth regulators which are quite slow to elicit effects.

The present inventors have found that the following parameters are important to yield compounds having the nucleus of Formula I which are insect growth regulators. A and B should have some bulk. However, if the bulk becomes too great, the compounds become less effective as insect growth regulators. Therefore, A and B should independently contain no more than about 21 non-hydrogen atoms.

The size of the moiety E of Formula I is important. E should have at least 4 non-hydrogen atoms. Oxygen containing radicals have been found to be generally not preferred. If oxygen is present, generally E should be bulkier. Moieties containing two oxygen atoms or one oxygen and one sulfur atom are less preferred. It is preferred that E have no greater than 10 non-hydrogen atoms. Preferably, E does not include a chain of greater than four or five non-hydrogen atoms but is highly branched.

The compounds of this invention or their precursors can be prepared according to the following processes. Process A can be used when preparing compounds according to Formula II below where X and X' are both oxygen and A and B are the same (for example, both A and B are phenyl or 4-chlorophenyl) or different (for example, A is 4-methylphenyl and B is 4-chlorophenyl). ##STR11## wherein A and B are organic radicals attached to the carbon shown in Formula II by a carbon-to-carbon single bond and R¹ is other than hydrogen. ##STR12## where R¹, A and B are as defined above for Formula II and X and X' are oxygen.

When R¹ is cyano substituted alkyl the intermediate Va may be made as follows: ##STR13## where M is K or Na, X and X' are oxygen, A and B are as defined above for Formula II, and R₃ and R₄ are the same or different hydrogen or (C₂ -C₉) straight or branched chain unsubstituted or substituted alkyl having one or two of the same or different (C₃ -C₆)cycloalkyl;

Process B can be used when preparing compounds according to Formula II where X and X' are oxygen, and R¹, A and B are as defined above for Formula II. ##STR14## where X and X' are oxygen, A and B are as defined above for Formula II, and R³ and R⁴ are the same or different hydrogen or (C₂ -C₉) straight or branched chain unsubstituted or substituted alkyl having one or two of the same or different (C₃ -C₆)cycloalkyl. As can be seen above, the intermediate product of Step 2, the compounds of Formula X, corresponds to the compounds of Formula V. In addition, the compound of Formula XI corresponds to the compounds of Formula II where X and X' are oxygen. ##STR15## where R¹, A and B are as defined above for Formula II and W is a good leaving group such as halo, for example, chloro; an alkoxy, for example, ethoxy; methyl sulfonate (--OSO₂ CH₃); or an ester, for example, acetate (--OC(O)CH₃).

Process C can be used when preparing compounds according to Formula II where A, B and R¹ are as defined for Formula II and one or both X and X' are sulfur. ##STR16## where A, B and R¹ are as defined above for Formula II and one or both X and X' are sulfur, and Y is a good leaving group such as carboxyalkylthio (for example, carboxymethylthio, --SCH₂ CO₂ H); alkylthio (for example, methylthio); or halo (for example, chloro).

Process D can be used when preparing compounds according to Formula II where X and X' are oxygen and R¹, A and B are as defined above for Formula II. ##STR17## wherein A, B and R¹ are as defined above for Formula II and Z is t-butyl; ethyl; phenyl; or benzyl.

The starting materials for each process are generally commercially available, or can be prepared by generally customary and known methods.

Other compounds of this invention or their precursors can be prepared by reacting a suitably substituted hydrazine (Formula II) with an alkyl halide, allyl halide or phenylmethylhalide in the presence of a base in an inert or substantially inert solvent or mixture of solvents according to the following process: ##STR18## where X, X', R¹, R², A and B are as defined above for Formula II and Hal is halogen (chloro, fluoro or bromo).

Suitable bases for use in the above process include metal hydrides such as sodium hydride or potassium hydride; metal alkoxides such as sodium alkoxides or potassium alkoxides; sodium hydroxide; potassium hydroxide; or lithium diisopropyl amide. If desired, mixtures of these bases may be used. The preferred base is potassium t-butoxide.

Suitable solvents for use in the above process include ethers such as tetrahydrofuran (THF), glyme and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; or a mixture of water and benzene or toluene. If desired, mixtures of these solvents may be used. The preferred solvent is dimethylformamide.

The above process can be carried out at temperatures between about -20° C. and about 100° C. Preferably, this reaction is carried out between about -5° C. and about 50° C.

Preparation of the compounds of the present invention by the above process is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired.

Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired.

Generally one equivalent of base is used per equivalent of starting material of Formula XXI.

The compounds of Formula XXI are generally commercially available or can be prepared by known procedures.

Modifications to the above process may be necessary to accommodate reactive functionalities of particular substituents. Such modifications would be apparent and known to those skilled in the art.

In process A, a compound of Formula III is reacted with a monosubstituted hydrazine of Formula IV or a corresponding acid addition salt such as the hydrochloride salt or the like in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford an intermediate product of Formula V which can be isolated or further reacted with a compound of Formula VI in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford the desired product of Formula II.

When A and B are the same, for example, both A and B are 4-chlorophenyl, two equivalents of a compound of Formula III or VI are reacted with a monosubstituted hydrazine of Formula IV in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford the desired product of Formula II.

Examples of the compounds of Formula III and/or Formula VI which can be used in the above processes include benzoyl chloride, 4-chlorobenzoyl chloride, 4-methylbenzoyl chloride, 3,5-dichlorobenzoyl chloride, 2-bromobenzoyl chloride, 3-cyanobenzoyl chloride, 3-toluoyl chloride, 4-toluoyl chloride, 4-ethylbenzoyl chloride, 2-nitrobenzoyl chloride, 2,3-dimethylbenzoyl chloride, 2-nitro-5-toluoyl chloride, cyclohexylcarbonyl chloride, n-butanoyl chloride, n-pentanoyl chloride, phenylacetyl chloride, 1-cyclohexenecarbonyl chloride, pivaloyl chloride, trichloroacetyl chloride, methacryloyl chloride and the like. The compounds of Formula III and/or Formula VI are generally commercially available or can be prepared by known procedures.

Examples of the compounds of Formula IV which can be used in the above processes include isopropylhydrazine, t-butylhydrazine, neopentylhydrazine, alphamethylneopentylhydrazine, isobutylhydrazine, isopentylhydrazine, isooctylhydrazine, 1,1-dimethyl-3-butenylhydrazine, (trimethylsilylmethyl)hydrazine, (1,1,1-trifluoro-2-propyl)hydrazine, (2,2,2-trifluoroethyl)hydrazine, (1-cyano-1-methyl)ethylhydrazine and the like. The compounds of Formula IV are generally commercially available or can be prepared by known procedures. For example, the Grignard reagent addition product of acetone azine in diethyl ether is hydrolyzed by the addition of an acid (such as oxalic acid), in a suitable solvent or mixture of solvents (such as ethanol and diethyl ether, 1:1) to afford the monosubstituted hydrazine of Formula IV.

Suitable solvents for use in the above processes include water; alcohols such as methanol, ethanol, isopropanol and the like; hydrocarbons such as toluene, xylene, hexane, heptane and the like; glyme; tetrahydrofuran; acetonitrile; pyridine; or haloalkanes such as methylene chloride or mixtures of these solvents.

Preferred solvents are water, toluene, methylene chloride or a mixture of these solvents.

Examples of bases for use in the above processes include tertiary amines such as triethylamine; pyridine; potassium carbonate; sodium carbonate; sodium bicarbonate; sodium hydroxide; or potassium hydroxide. Preferred bases are sodium hydroxide, potassium hydroxide or triethylamine.

In Process B, Method 1, a compound of Formula VII is reacted with a ketone or aldehyde of Formula VIII in an inert or substantially inert solvent or mixture of solvents and optionally in the presence of a catalyst to afford an intermediate product of Formula IX. The intermediate product of Formula IX is then further reacted with a reducing agent in an inert or substantially inert solvent or mixture of solvents to afford a second intermediate product of Formula X which can be isolated or further reacted with a compound of Formula VI in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford the desired product of Formula XI.

Examples of the compounds of Formula VII which can be used in the above Process B, Method 1, include benzoylhydrazine, 4-chlorobenzoylhydrazine, 2-methylbenzoylhydrazine, 4-methylbenzoylhydrazine, 3,5-dichlorobenzoylhydrazine and the like. The compounds of Formula VII are generally commercially available or can be prepared by known procedures.

Examples of the compounds of Formula VIII which can be used in the above Process B, Method 1, include 1,1,1-trimethylacetaldehyde, methylethylketone, diethylketone, trifluoroacetone, methacrolein, ethyl pyruvate and the like. The compounds of Formula VIII are generally commercially available or can be prepared by known procedures.

Optionally, a catalyst may be used in Step 1, Method 1 of Process B. Suitable catalysts generally include organic acids such as acetic acid, trifluoroacetic acid, oxalic acid and the like; mineral acids such as hydrochloric acid, sulfuric acid, nitric acid and the like; arylsulfonic acids such as toluenesulfonic acid; or pyridinium toluenesulfonate. Preferred catalysts are organic acids or arylsulfonic acids. Most preferred catalysts are acetic acid or trifluoroacetic acid.

Suitable solvents for use in the above Process B, Method 1, Step 1, include alcohols such as methanol, ethanol, isopropanol and the like; hydrocarbons such as toluene, benzene; ethers such as tetrahydrofuran (THF), glyme and the like; or dimethylformamide. Preferred solvents are alcohols and hydrocarbons. Most preferred solvents are alcohols such as methanol or ethanol.

Examples of suitable reducing agents for use in the above Process B, Method 1, Step 2, include hydrides such as sodium borohydride and derivatives thereof such as sodium cyanoborohydride, lithium aluminum hydride and derivatives thereof and the like; or diborane. Preferred reducing agents are sodium borohydride and derivatives thereof or lithium aluminum hydride and derivatives thereof. Most preferred as reducing agents are borane and diborane.

Optionally, in Process B, Method 1, Step 2, a catalyst may be included. Examples of suitable catalysts include organic acids such as acetic acid, trifluoroacetic acid; or mineral acids such as hydrochloric acid, sulfuric acid and the like. Preferred catalysts are organic acids or hydrochloric acid. Most preferred catalysts are acetic acid, trifluoroacetic acid or hydrochloric acid.

Suitable solvents for use in the above Process B, Method 1, Step 2, include alcohols such as methanol, ethanol, isopropanol and the like; ethers such as tetrahydrofuran (THF), diethylether, glyme and the like; or halohydrocarbons such as methylene chloride, chloroform and the like. Preferred solvents are alcohols and most preferred are methanol or ethanol.

Step 3 of Process B, Method I corresponds to Step 2 of Process A. Consequently, those bases and solvents suitable for use in Step 2 of Process A are suitable for use in Step 3, Method 1 of Process B including the preferred bases and solvents described above.

In Process B, Method 2, N'-substituted-N'-benzoylhydrazine of Formula XIII or N'-substituted-N-benzoylhydrazine of Formula XIIIa is reacted with a compound of Formula XII in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford the desired product of Formula II.

The compounds of Formula XII are generally commercially available or can be prepared from commercially available compounds by procedures well known to those skilled in the art as described below.

Examples of the compounds of Formula XIII which can be used in the above Process B, Method 2, include N'-t-butyl-N'-benzoylhydrazine; N'-t-butyl-N'-(3-methylbenzoyl)hydrazine; N'-t-butyl-N'-(4-chlorobenzoyl)hydrazine; N'-t-butyl-N'-(2-fluorobenzoyl)hydrazine; N'-isopropyl-N'-benzoylhydrazine; N'-neopentyl-N'-(4-chlorobenzoyl)hydrazine, N'-isopropyl-N-benzoylhydrazine; N'-sec-butyl-N-benzoylhydrazine; N'-(1-methyl)neopentyl-N-benzoylhydrazine; N'-neopentyl-N-benzoylhydrazine; N'-isobutyl-N-benzoylhydrazine; N'-(1,2,2-trimethylpropyl)-N-benzoylhydrazine; N'-diisopropylmethyl-N-benzoylhydrazine; N'-t-butyl-N-benzoylhydrazine; N'-t-butyl-N-(4-methylbenzoyl)hydrazine; N'-t-butyl-N-(4-chlorobenzoyl)hydrazine; N'-(1,1-dimethyl-3-butenyl)-N'-benzoylhydrazine, N'-(trimethylsilylmethyl)-N'-(4-methylbenzoyl)hydrazine, N'-(1,1,1-trifluoro-2-propyl)-N'-(2,4-dichlorobenzoyl)hydrazine, N'-(1-cyano-1-methyl)ethyl-N'-(2-methylbenzoyl)hydrazine and the like.

Suitable solvents for use in the above Process B, Method 2, include water; hydrocarbons such as toluene, xylene, hexane, heptane and the like; alcohols such as methanol, ethanol, isopropanol, and the like; glyme; tetrahydrofuran; acetonitrile; pyridine; or haloalkanes such as methylene chloride; or mixtures of these solvents. Preferred solvents are water, toluene, methylene chloride or a mixture of these solvents.

Examples of bases suitable for use in the above Process C includes tertiary amines such as triethylamine; pyridine; potassium carbonate; sodium carbonate; sodium bicarbonate; sodium hydroxide; or potassium hydroxide. Preferred bases are sodium hydroxide, or triethylamine.

The compounds of Formula XII are commercially available, such as nicotinoyl chloride hydrochloride, isonicotinoyl chloride hydrochloride and ethyl picolinate or can be prepared from commercially available materials by procedures known to those skilled in the art.

The compounds of Formula XIII can be prepared by procedures known to those skilled in the art from commercially available reactants. By way of example, a suitably substituted hydrazine (such as t-butyl-hydrazine or (1,1,1-trifluoro-2-propyl)hydrazine) is reacted with an aldehyde or ketone (such as acetone) in the presence of a base (such as triethylamine) to afford a hydrazone which is then reacted with a benzoyl chloride in an inert or substantially inert solvent or mixture of solvents in the presence of a base (such as sodium hydroxide) to afford an N'-substituted-N'-benzoylhydrazone which is then reacted with an acid (such as hydrochloric acid) to afford the compound of Formula XIII. Alternatively, a suitable substituted hydrazine (such as t-butyl-hydrazine or (trimethylsilylmethyl)hydrazine) is reacted with di-tert-butyldicarbonate in an inert or substantially inert solvent or mixture of solvents (such as toluene/water) to afford an N'-t-butyl-N-t-butoxycarbonylhydrazine or an N'-(trimethylsilylmethyl)-N-t-butoxycarbonylhydrazine which is then reacted with a benzoylchloride in an inert or substantially inert solvent or mixture of solvents to afford N'-t-butyl-N'-benzoyl-N-t-butoxycarbonylhydrazine or an N'-(trimethylsilylmethyl)-N'-benzoyl-N-t-butoxycarbonylhydrazine which is then reacted with an acid to afford the desired compound of Formula XIII.

In Process C, a compound of Formula XIV is reacted with a monosubstituted hydrazine of Formula IV or a corresponding acid addition salt such as the hydrochloride salt or the like in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford an intermediate compound of Formula XV which can be isolated or further reacted with a compound of Formula XVI in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford the desired product of Formula I.

In Process D, a monosubstituted hydrazine of Formula IV or a corresponding acid addition salt, such as the hydrochloride salt or the like, is reacted with a compound of Formula XVII in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford an intermediate product of Formula XVIII. The intermediate product of Formula XVIII is then further reacted with a compound of Formula VI in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford a second intermediate product of Formula XIX. The second intermediate product of Formula XIX is then further reacted with an acid in an inert or substantially inert solvent or mixture of solvents to afford a third intermediate product of Formula XX. The third intermediate product of Formula XX is then further reacted with a compound of Formula III in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford the desired product of Formula II.

Examples of the compounds of Formula XVII which can be used in the above Process D include di-t-butyldicarbonate, diethyldicarbonate, diphenyldicarbonate, dibenzyldicarbonate and the like. The compounds of Formula XVII are generally commercially available or can be prepared by known procedures.

Suitable solvents for use in the above Process D, Steps 1, 2 and 4 include water; tetrahydrofuran; dioxane; toluene; alcohols such as methanol, ethanol and isopropanol; hexane; acetonitrile; pyridine; and haloalkanes such as methylene chloride; or mixtures of these solvents.

Preferred solvents are dioxane; toluene; tetrahydrofuran; pyridine; methylene chloride or water.

Most preferred solvents are dioxane; water or toluene.

Examples of the bases for use in the above Process D, Steps 1, 2 and 4 include tertiary amines such as triethylamine; pyridine; potassium carbonate, sodium carbonate; sodium bicarbonate; sodium hydroxide; and potassium hydroxide.

Preferred bases are sodium hydroxide; potassium hydroxide; pyridine or triethylamine.

Suitable solvents for use in the above Process D, Step 3 include alcohols such as methanol, ethanol and isopropanol; water; tetrahydrofuran; dioxane; and acetonitrile.

Preferred solvents are methanol or ethanol.

Examples of acids for use in the above Process D, Step 3 include concentrated hydrochloric acid or concentrated sulfuric acid.

When A and B are the same, for example, both A and B are unsubstituted phenyl, two equivalents of a compound Formula XIV or XVI are reacted with a monosubstituted hydrazine of Formula IV in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford the desired product of Formula II.

Examples of the compounds of Formula XIV and/or Formula XVI which can be used in the above Process C include 3-methyl-methylthio-thiobenzoate, 4-chloromethylthio-thiobenzoate, 4-methyl-methylthio-thiobenzoate, carboxymethylthiothiobenzoate and the like. The compounds of Formula XIV and/or Formula XVI are generally commercially available or can be prepared by known procedures.

Suitable solvents for use in the above Process C are generally polar high-boiling solvents such as dimethylformamide (DMF); glyme; tetrahydrofuran (THF); and pyridine. The preferred solvent is pyridine.

Suitable bases for use in the above Process C include tertiary amines such as triethylamine; and pyridine. The preferred base is pyridine.

The above Processes A and B, Method 1, can be carried out at temperatures between about -20° C. and about 100° C. Preferably, these reactions are carried out between about -5° C. and about 50° C.

The above Process B, Method 2, can be carried out at temperatures between about -50° C. and about 150° C. Preferably when W is a halo radical, the reaction is carried out between about 0° C. and about 30° C. When W is alkoxy, the reaction is preferably carried out between about 100° C. and about 150° C. When W is methyl sulfonate, the reaction is preferably carried out between about -20° C. to about 20° C. When W is an ester, the reaction is preferably carried out between about 0° C. and about 50° C.

Process C can be carried out at temperatures between about 10° C. and 200° C. Preferably, this reaction is carried out between about 70° C. and about 100° C.

Process D can be carried out at temperatures between about 0° C. and 100° C. Preferably, these reactions are carried out between about 0° C. and about 50° C.

Preparation of the compounds of the present invention by processes A, B, C and D are preferably carried out at about atmospheric pressure, although higher or lower pressures can be used if desired.

Substantially equimolar amounts of reactants are preferably used in processes A, B and C, although higher or lower amounts can be used if desired.

Generally, about one equivalent of base is used per equivalent of starting material of Formula III, VI, XII and/or XIV. Where the acid addition salt of the monosubstituted hydrazine of Formula IV is used, one additional equivalent of base is used. For example, in Process A, when substituents A and B are the same and a monosubstituted hydrazine is used, about two equivalents of base are used since about two equivalents of a suitably substituted benzoyl chloride of Formula III or VI are employed. In Process A, when substituents A and B are different and an acid addition salt of the monosubstituted hydrazines of Formula IV is used, about two equivalents of base are used in Step 1 and about one equivalent of base is used in Step 2.

Modifications to the above processes may be necessary to accommodate reactive functionalities of particular A and/or B substituents. Such modifications would be apparent and known to those skilled in the art.

It will be appreciated by those skilled in the art that electronic forces may give rise to more than one isomer of the compounds of Formula II such as enantiomers, conformers and the like. There may be a difference in properties such as physical characteristics and degree of biological activity between such isomers. Separation of a specific isomer can be accomplished by standard techniques well known to those skilled in the art such as silica gel chromatography.

The agronomically acceptable salts embraced by Formula I of the invention can be prepared by reacting a metal hydroxide, a metal hydride or an amine or ammonium salt, such as a halide, hydroxide or alkoxide with a compound of Formula I having one or more hydroxy or carboxy groups or reacting a quaternary ammonium salt, such as chloride, bromide, nitrate or the like with a metal salt of a compound of Formula I in a suitable solvent. When metal hydroxides are used as reagents, useful solvents include water; ethers such as glyme and the like; dioxane; tetrahydrofuran; alcohols such as methanol, ethanol, isopropanol and the like. When metal hydrides are used as reagents, useful solvents include nonhydroxylic solvents, for example, ethers such as dioxane, glyme, diethylether and the like; tetrahydrofuran; hydrocarbons such as toluene, xylene, hexane, pentane, heptane, octane and the like; dimethylformamide, and the like. When amines are used as reagents, useful solvents include alcohols, such as methanol or ethanol; hydrocarbons, such as toluene, xylene, hexane and the like; tetrahydrofuran; glyme; dioxane; or water. When ammonium salts are used as reagents, useful solvents include water; alcohols, such as methanol or ethanol; glyme; tetrahydrofuran; or the like. When the ammonium salt is other than a hydroxide or alkoxide, an additional base, such as potassium or sodium hydroxide, hydride, or alkoxide is generally used. The particular choice of solvent will depend on the relative solubilities of the starting materials and the resultant salts, and slurries rather than solutions of certain reagents may be used to obtain the salts. Generally, equivalent amounts of the starting reagents are used and the salt-forming reaction is carried out at about 0° C. to about 100° C., preferably at about room temperature.

The acid addition salts of the present invention can be prepared by reacting hydrochloric, hydrobromic, sulfuric, nitric, phosphoric, acetic, propionic, benzoic or other suitable acid with a compound of Formula I having a basic functional group in a suitable solvent. Useful solvents include water, alcohols, ethers, esters, ketones, haloalkanes and the like. The particular choice of solvent will depend on the relative solubilities of the starting materials and the resulting salts and slurries rather than solutions of certain reagents may be used to obtain the salts. Generally, equivalent molar amounts of starting materials are used and the salt-forming reaction is carried out at from about -10° C. to about 100° C., preferably at about room temperature.

The following examples will further illustrate this invention but are not intended to limit it in any way. In Table I, some N'-substituted-N,N'-disubstitutedhydrazines of the present invention that have been made are listed. The structure of these compounds was confirmed by NMR and in some cases by IR and/or elemental analysis. Specific illustrative preparation of the compounds of Examples 1, 3, 16, 44, 102, 103, 148, 220, 295, 324, 625, 635, 636, 637, 638, 639, 642, 646, 648, 654, 656, 659, 660, 682, 683, 688, 689, 691, 699, 702, 722, 723, 724, 727, 729, 733, 737, 738, 739, 743, 754, 755, 764, 765, 766, 767, 772, 778, 787, 802, 809, 822, 829, 837, 853, 855, 864, 870 to 873, 878, 880, 882, 883, 893, 905, 914, 918, 922, 923, 933, 941, 942, 944, 948, 1002, 1008, 1013 and 1015 to 1018 are described after Table I.

                                      TABLE I                                      __________________________________________________________________________       #STR19##                                                                        -                                                                           Ex.                                                                              # C(X) C(X') E F A' B'                                                       __________________________________________________________________________      1  C(O)       C(O)                                                                              --C(CH.sub.3).sub.3                                                                        H      --C.sub.6 H.sub.4 Cl-4                                                                      --C.sub.6 H.sub.4 Cl-4                                                           2 C(O) C(O) --C(CH.sub                                                       .3).sub.3 H --C.sub.6                                                          H.sub.4 Cl-3 --C.sub.6                                                         H.sub.4 Cl-3                    3 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.5                                                           4 C(O) C(O) --C(CH.sub                                                       .3).sub.3 H --C.sub.6                                                          H.sub.3 Cl.sub.2 -3,4                                                          --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,4                   5 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                               --C.sub.6 H.sub.4                                                              CH.sub.3 -4                     6 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 NO.sub.2 -4                                                               --C.sub.6 H.sub.4                                                              NO.sub.2 -4                     7 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCH.sub.3 -4                                                              --C.sub.6 H.sub.4                                                              OCH.sub.3 -4                    8 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 NO.sub.2 -3                                                               --C.sub.6 H.sub.4                                                              NO.sub.2 -3                     9 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCH.sub.3 -3                                                              --C.sub.6 H.sub.4                                                              OCH.sub.3 -3                    10 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 NO.sub.2 -2                                                              --C.sub.6 H.sub.4                                                              NO.sub.2 -2                     11 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-2 --C.sub.6                                                           H.sub.4 Cl-2                    12 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCH.sub.3 -2                                                             --C.sub.6 H.sub.4                                                              OCH.sub.3 -2                    13 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                              --C.sub.6 H.sub.5                                                                14 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CN-4 --C.sub.6                                                         H.sub.4 CN-4                    15 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                              --C.sub.6 H.sub.4 Cl-4                                                           16 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 Cl-4                    17 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        Cl-3                            18 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        Cl-2                            19 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -3                                                              --C.sub.6 H.sub.4                                                              CH.sub.3 -3                     20 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -2                                                              --C.sub.6 H.sub.4                                                              CH.sub.3 -2                     21 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        CH.sub.3 -4                     22 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        CH.sub.3 -3                     23 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        CH.sub.3 -2                     24 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        OCH.sub.3 -4                    25 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        OCH.sub.3 -3                    26 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        OCH.sub.3 -2                    27 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        C(CH.sub.3).sub.3 -4                                                             28 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 CN-4                    29 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        NO.sub.2 -4                     30 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        NO.sub.2 -3                     31 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        NO.sub.2 -2                     32 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 C(CH.sub.3).sub.3                                                        -4 --C.sub.6 H.sub.4                                                           C(CH.sub.3).sub.3 -4                                                             33 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.3 -4                                                            --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,4                   34 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        F-4                             35 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        F-3                             36 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        F-2                             37 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl.sub.2 -3,5                                                            --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,5                   38 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        Cl.sub.2 -2,4                   39 C(O) C(O) --CH(CH.sub.3).sub.2 H --C.sub.6 H.sub.5 --C.sub.6                                                               H.sub.5                         40 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        CF.sub.3 -4                     41 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        CF.sub.3 -3                     42 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        CF.sub.3 -2                     43 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        F.sub.2 -2,5                    44 C(O) C(O) --CH.sub.2 C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                        H.sub.5                        45 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        CN-3                            46 C(O) C(O) CH(CH.sub.3)C.sub.2 H.sub.5 H --C.sub.6 H.sub.5 --C.sub.6                                                        H.sub.5                         47 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        F.sub.2 -2,6                    48 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 --C.sub.6                                                           H.sub.5                         49 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        Cl.sub.2 -3,4                   50 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        Cl.sub.2 -3,5                   51 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        Cl.sub.2 -2,6                   52 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 C(CH.sub.3).sub.3                                                        -4 --C.sub.6 H.sub.5                                                             53 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.5                         54 C(O) C(O) --C(CH.sub.3).sub.3 H 1-naphthyl --C.sub.6 H.sub.5                                                                 55 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 1-naphthyl                                                        1-naphthyl                      56 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-3 --C.sub.6                                                           H.sub.5                         57 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 --C.sub.6                                                           H.sub.3 Cl.sub.2 -3,4                                                            58 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.3 Cl.sub.2 -3,4                                                            59 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.3 -2                                                            --C.sub.6 H.sub.5                                                                60 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.3 Cl-2-NO.sub.2                                                          -4                              61 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        (NO.sub.2).sub.2 -3,5                                                            62 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.3 Cl.sub.2 -2,3                                                            -  63 C(O) C(O)                                                                H --C.sub.6 H.sub.5                                                          --C.sub.6 H.sub.5                                                                -  64 C(O) C(O)                                                              --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.3                                                              Cl-2-CH.sub.3 -5                                                                 65 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.3 (CH.sub.3).sub.2                                                        -3,5                           66 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        NO.sub.2 -2-CH.sub.3 -5         67 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        CH.sub.3 -2-Cl-3                                                                 68 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.3 Cl-3-CH.sub.3                                                          -4                              69 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        NO.sub.2 -2-Cl-3                                                                 70 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.3 OCH.sub.3                                                              -3-NO.sub.2 -4                  71 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        NO.sub.2 -2-OCH.sub.3                                                          -3                              72 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 C.sub.6 H.sub.3                                                          (NO.sub.2).sub.2 -2,4                                                            73 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-4 --C.sub.6                                                         H.sub.4 Cl-2                    74 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 --C.sub.6                                                           H.sub.4 Cl-3                    75 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 --C.sub.6                                                           H.sub.4 CH.sub.3 -4                                                              76 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-4 --C.sub.6                                                         H.sub.3 Cl.sub.2 -3,5                                                            77 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-4 --C.sub.6                                                         H.sub.3 Cl.sub.2 -2,4                                                            78 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-4 --C.sub.6                                                         H.sub.4 CF.sub.3 -4                                                              79 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 OSO.sub.2                                                              CH.sub.3 -4                     80 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        CH(CH.sub.3).sub.2 -4                                                            81 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 OCOCH.sub.3 -2                                                           82 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 CH.sub.2                                                               CH.sub.3 -4                     83 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        Br-2                            84 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        OH-4                            85 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                              --C.sub.6 H.sub.4                                                              CH.sub.3 -2                     86 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                              --C.sub.6 H.sub.4                                                              CH.sub.3 -3                     87 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                              --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                   88 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                              --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,5                   89 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                              --C.sub.6 H.sub.4 Cl-2                                                           90 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.3 -4                                                            --C.sub.6 H.sub.4 F-4                                                            91 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.3 -4                                                            --C.sub.6 H.sub.4                                                              CF.sub.3 -4                     92 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                              --C.sub.6 H.sub.4 Cl-3                                                           93 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-4 --C.sub.6                                                         H.sub.4 CH.sub.2 Cl-3                                                            94 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-4 --C.sub.6                                                         H.sub.4 CH.sub.2 Cl-4                                                            95 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-4 --C.sub.6                                                         H.sub.4 CH.sub.3 -2                                                              96 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-4 --C.sub.6                                                         H.sub.4 OCH.sub.3 -3                                                             97 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-4 --C.sub.6                                                         H.sub.4 CH.sub.3 -3                                                              98 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 F-4 --C.sub.6                                                          H.sub.4 F-4                     99 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 F-3 --C.sub.6                                                            H.sub.4 F-3                    100 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 F-2 --C.sub.6                                                            H.sub.4 F-2                    101 C(O) C(O) --C(CH.sub.3).sub.3 H 2-naphthyl 2-naphthyl                      102 C(S) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 --C.sub.6                                                           H.sub.5                        103 C(O) C(S) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.5        104 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        Br-4                           105 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        Br-3                           106 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 4-butylphenyl                                                             107 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2                                                               CH.sub.3 -4 --C.sub.6                                                          H.sub.5                        108 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl.sub.2 -3,4                                                            --C.sub.6 H.sub.5                                                               109 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 COCH.sub.3 -4                                                           110 C(O) C(O) --CH.sub.                                                       2 C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.4 Br-2                                                          111 C(O) C(O) --CH.sub.                                                       2 C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              C.sub.6 H.sub.4                                                                NO.sub.2 -2                    112 C(O) C(O) --CH.sub.2 C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                        H.sub.4 OCH.sub.3 -2                                                           113 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 I-2                    114 C(O) C(O) CH.sub.2 CH(CH.sub.3).sub.2 H --C.sub.6 H.sub.5 --C.sub.6                                                        H.sub.5                        115 C(O) C(O) --CH(CH.sub.3).sub.2 H --C.sub.6 H.sub.5 --C.sub.6                                                               H.sub.4 Br-2                   116 C(O) C(O) --CH(CH.sub.3).sub.2 H --C.sub.6 H.sub.5 --C.sub.6                                                               H.sub.3 Cl.sub.2 -3,4                                                           117 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 OC.sub.6                                                               H.sub.5 -4                     118 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CF.sub.3 -4                                                              --C.sub.6 H.sub.5                                                               119 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CF.sub.3 -4                                                            --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,4                  120 C(O) C(O) --CH H --C.sub.6 H.sub.5 --C.sub.6 H.sub.5                       121 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        Cl-2-Br-4                      122 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        C.sub.6 H.sub.5 -4                                                              123 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.2 (OCH.sub.3).sub.                                                       3 -3,4,5                        - 124 C(O) C(O)                                                                                                                 H --C.sub.6 H.sub.5                                                          --C.sub.6 H.sub.4                                                              NO.sub.2 -2                     - 125 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                             H.sub.4 CH.sub.2 SCN-3                                                          126 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 CH.sub.2 CN-3                                                            - 127 C(O) C(O)                                                                H --C.sub.6 H.sub.5                                                          --C.sub.6 H.sub.5                                                                - 128 C(O) C(O)                                                              CH[CH(CH.sub.3).sub.2                                                          ].sub.2 H --C.sub.6                                                            H.sub.5 --C.sub.6                                                              H.sub.5                        129 C(O) C(O) 1-cyclopropyl H --C.sub.6 H.sub.5 --C.sub.6 H.sub.5                                                                  ethyl                      130 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.4                                                           CH.sub.3 -3                    131 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.4                                                           Cl-4                           132 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.4                                                           NO.sub.2 -2                    133 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        CH.sub.2 CH.sub.3 -3                                                            134 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2                                                               CH.sub.3 -4 --C.sub.6                                                          H.sub.4 Br-3                   135 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.4                                                           I-2                             - 136 C(O) C(O)                                                                                                                 H --C.sub.6 H.sub.5                                                          --C.sub.6 H.sub.4 Br-2                                                           - 137 C(O) C(O)                                                              --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.4                                                              CO.sub.2 CH.sub.3 -4                                                            138 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Br-2 --C.sub.6                                                         H.sub.5                        139 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CF.sub.3 -2                                                              --C.sub.6 H.sub.5                                                               140 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 I-3                    141 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        CH.sub.2 CH.sub.3 -2                                                            142 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 CH.sub.2                                                               OCH.sub.3 -3                   143 C(O) C(O) 1-cyclohexyl H --C.sub.6 H.sub.5 --C.sub.6 H.sub.5                                                                   ethyl                      144 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 C.sub.6 H.sub.4                                                          OCH.sub.2 CH═CH.sub.                                                       2 -4                           145 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 C.sub.6 H.sub.5                                                          -4 --C.sub.6 H.sub.4                                                           C.sub.6 H.sub.5 -4                                                              146 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 2-nitro-5-(2-chl                                                       oro-                                 4-trifluoromethyl                                                              phenoxy)phenyl                                                           147 C(O) C(O) --C(CH.sub.3).sub.3 H 2-nitro-5-(2-chloro- --C.sub.6                                                             H.sub.5                             4-trifluoromethyl                                                              phenoxy)phenyl                                                            148 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 (CH.sub.2 OC(O)C.sub                                                       .6 --C.sub.6 H.sub.5                                                                 H.sub.5)-2                                                                149 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 SO.sub.2                                                               CH.sub.3 -4                    150 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        OH-2                           151 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        SCH.sub.3 -4                   152 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        Br-3-CH.sub.3 -4                                                                153 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.3 CH.sub.3                                                               -3-Br-4                        154 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        Br.sub.2 -2,4                  155 C(O) C(O) --CH(CH.sub.3).sub.2 H --C.sub.6 H.sub.5 --C.sub.6                                                               H.sub.3 Cl.sub.2 -2,6                                                           156 C(O) C(O) --CH.sub.                                                       2 C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,4                   - 157 C(O) C(O)                                                                                                                 H --C.sub.6 H.sub.5                                                          --C.sub.6 H.sub.4 CN-4                                                           - 158 C(O) C(O)                                                              --CH.sub.2 C(CH.sub.3).s                                                       ub.3 H --C.sub.6                                                               H.sub.5 --C.sub.6                                                              H.sub.4 CH.sub.2                                                               CH.sub.3 -4                    159 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --CH.sub.2 S--                                                           --CH.sub.3                     160 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        OC.sub.6 H.sub.5 -3                                                             161 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 (CH.sub.2                                                              OC(O)CH.sub.3)-3                                                                162 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 CH.sub.2 OH-4                                                           163 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 CHO-4                  164 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        CO.sub.2 H.sub.4                                                                 - 165 C(O) C(O)                                                                H --C.sub.6 H.sub.5                                                          --C.sub.6 H.sub.4 OH-2                                                           - 166 C(O) C(O)                                                              --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.4                                                              CH═CCl.sub.2 -4                                                              - 167 C(O) C(O)                                                                H --C.sub.6 H.sub.5                                                          --C.sub.6 H.sub.4                                                              (OC(0)CH.sub.3)-2                                                                - 168 C(O) C(O)                                                              --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.3                                                              (OCH.sub.3).sub.2 -3,4                                                         --C.sub.6 H.sub.5                                                               169 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2 Cl-2                                                          --C.sub.6 H.sub.4                                                              CH.sub.2 Cl-2                  170 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 CH.sub.2 Cl-2                                                              --C.sub.6 H.sub.5                                                               171 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 NO.sub.2 -2                                                            --C.sub.6 H.sub.5                                                               172 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H C.sub.6                                                           H.sub.4 CH.sub.2                                                               CH.sub.2 C.sub.H 3-4                                                           --C.sub.6 H.sub.5                                                               173 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 CH.sub.3                                                               -2-CF.sub.3 -5 --C.sub.6                                                        H.sub.4 CH.sub.3 -2                                                            174 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Br-2 --C.sub.6                                                         H.sub.4 Br-2                   175 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.4                                                           CH.sub.2 CH.sub.3 -3                                                            176 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 CH.sub.2                                                               CH.sub.2 CH.sub.3 -4                                                            177 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.3 -4                                                            --C.sub.6 H.sub.4 Br-3                                                          178 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.3 -4                                                            --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           179 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 I-4                    180 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                              --C.sub.6 H.sub.4                                                              CH.sub.2 CH.sub.3 -4                                                            181 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2                                                               CH.sub.3 -4 --C.sub.6                                                          H.sub.4 CH.sub.2                                                               CH.sub.3 -4                    182 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                              --C.sub.6 H.sub.4                                                              CH.sub.2 CH.sub.3 -3                                                            183 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 C.sub.6 H.sub.4                                                        CH(CH.sub.3).sub.2 -2                                                           184 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2                                                               CH.sub.3 -3 --C.sub.6                                                          H.sub.5                         - 185 C(O) C(O)                                                                                                                 H --C.sub.6 H.sub.5                                                          --C.sub.6 H.sub.4                                                              NO.sub.2 -3                     - 186 C(O) C(O) --CH.sub.2 C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.4                                                              NO.sub.2 -3                    187 C(O) C(O) --CH.sub.2 C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                        H.sub.4 CH.sub.3 -3                                                            188 C(O) C(O) --CH.sub.                                                       2 C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.4 Cl-4                                                          189 C(O) C(O) --CH.sub.                                                       2 C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.3                                                              (NO.sub.2).sub.2 -2,4                                                           190 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2                                                               CH.sub.3 -4 --C.sub.6                                                          H.sub.3 Cl.sub.2 -2,4                                                           191 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl.sub.2 -314                                                          --C.sub.6 H.sub.4 Cl-4                                                          192 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 (CH.sub.2).sub.6                                                        CH.sub.3 -4 --C.sub.6                                                         H.sub.4 Cl-4                   193 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 CH.sub.2 CH.sub.2                                                          CH.sub.3 -4 --C.sub.6                                                          H.sub.4 Cl-4                   194 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCH.sub.3 -4                                                             --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    195 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCH.sub.3 -4                                                             --C.sub.6 H.sub.5                                                               196 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.4 CH.sub.3 -3                                                             197 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.4 NO.sub.2 -2                                                             198 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.4 CH.sub.3 -4                                                             199 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.4 CH.sub.2                                                               CH.sub.3 -4                    200 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.3                                                           (CH.sub.3).sub.2 -3,5                                                           201 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2                                                               CH.sub.3 -4 --C.sub.6                                                          H.sub.3 CH.sub.3                                                               -3-Cl-6                        202 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        (OC(O)CH.sub.3)-3                                                               203 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 OH-3                   204 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.3                                                           NO.sub.2 -2-CH.sub.3 -3        205 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCH.sub.3 -4                                                             --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           206 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 OCH.sub.3 -4                                                           --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  207 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-2 --C.sub.6                                                           H.sub.3 Cl.sub.2 -2,6                                                           208 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.4 Br-2                   209 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-2 --C.sub.6                                                           H.sub.3 F.sub.2 -2,5                                                            210 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.4 OCH.sub.3 -4                                                            211 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.4 CH.sub.3 -2                                                             212 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 F-2 --C.sub.6                                                          H.sub.4 Cl-4                   213 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl.sub.2 -2,4                                                            --C.sub.6 H.sub.4 Cl-4                                                          214 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.3 Cl.sub.2 -2,4                                                           215 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.4 OCH.sub.3 -3                                                            216 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.4 Cl-3                   217 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-2 --C.sub.6                                                           H.sub.4 CF.sub.3 -2                                                             218 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.4 CF.sub.3 -3                                                             219 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.4 CF.sub.3 -4                                                             220 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.3 -3                                                            --C.sub.6 H.sub.5                                                               221 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 NO.sub.2 -3                                                            --C.sub.6 H.sub.5                                                               222 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl.sub.2 -2,6                                                          --C.sub.6 H.sub.5                                                               223 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F.sub.2 -2,4                                                           --C.sub.6 H.sub.5                                                               224 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.4 CN-4                   225 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-2 --C.sub.6                                                           H.sub.4 F-4                    226 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-2 --C.sub.6                                                           H.sub.4 Br-4                   227 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-2 --C.sub.6                                                           H.sub.4 Cl-4                   228 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-2 --C.sub.6                                                           H.sub.4 OCH.sub.3 -2                                                            229 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.4 NO.sub.2 -4                                                             230 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-2 --C.sub.6                                                         H.sub.4 F-2                    231 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-2 --C.sub.6                                                           H.sub.3 F.sub.2 -2,6                                                            232 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 NO.sub.2 -4                                                            --C.sub.6 H.sub.5                                                               233 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CN-4 --C.sub.6                                                         H.sub.5                        234 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCH.sub.3 -3                                                             --C.sub.6 H.sub.4                                                              OCH.sub.3 -3                   235 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCH.sub.3 -3                                                             --C.sub.6 H.sub.5                                                               236 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 OCH.sub.3 -3                                                           --C.sub.6 H.sub.4 Cl-4                                                          237 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 OCH.sub.3 -3                                                           --C.sub.6 H.sub.4                                                              Cl.sub.2 -3,4                  238 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 OCH.sub.3 -2                                                               --C.sub.6 H.sub.5                                                               239 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 OCH.sub.3 -2                                                           --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    240 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 OCH.sub.3 -2                                                               --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,4                  241 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCH.sub.3 -2                                                             --C.sub.6 H.sub.4 Cl-4                                                          242 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 OCH.sub.3 -2                                                           --C.sub.6 H.sub.4                                                              NO.sub.2 -2                    243 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        OCF.sub.3 -4                   244 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCF.sub.3 -4                                                             --C.sub.6 H.sub.5                                                               245 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 OCF.sub.3 -4                                                           --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    246 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCF.sub.3 -4                                                             --C.sub.6 H.sub.4 Cl-4                                                          247 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 OCF.sub.3 -4                                                           --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,4                  248 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CF.sub.3 -4                                                              --C.sub.6 H.sub.4 Cl-4                                                          249 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CF.sub.3 -4                                                            --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    250 C(O) C(O) C(CH.sub.3).sub.2 CH.sub.2 C H --C.sub.6 H.sub.5 --C.sub.6                                                        H.sub.5                          H.sub.2 CH.sub.2 CH.sub.3                                                   251 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCH.sub.2                                                                CH.sub.3 -4 --C.sub.6                                                          H.sub.4 CH.sub.3 -3                                                             252 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 OCH.sub.2                                                              CH.sub.3 -4 --C.sub.6                                                          H.sub.3 (CH.sub.3).sub.2                                                        -3,5                          253 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCH.sub.2                                                                CH.sub.3 -4 --C.sub.6                                                          H.sub.5                        254 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.3                                                           NO.sub.2 -2-Cl-4                                                                255 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl-3-OCH.sub.3                                                         -4 --C.sub.6 H.sub.5                                                            256 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 SCH.sub.3 -4                                                           --C.sub.6 H.sub.5                                                               257 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H C.sub.6                                                           H.sub.4 OCH.sub.2                                                              CH.sub.2 CH --C.sub.6                                                          H.sub.4 Cl-4                        .sub.2 CH.sub.3 -4                                                        258 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 SCH.sub.3 -2                                                             --C.sub.6 H.sub.5                                                               259 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 NO.sub.2                                                               -2-Cl-4 --C.sub.6                                                              H.sub.5                        260 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 NO.sub.2 -2-Cl-4                                                         --C.sub.6 H.sub.3                                                              NO.sub.2 -2-Cl-4                                                                261 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 NO.sub.2                                                               -2-Cl-4 --C.sub.6                                                              H.sub.4 C(CH.sub.3).sub.                                                       3 -4                           262 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 NO.sub.2 -2-Cl-4                                                         --C.sub.6 H.sub.4 Cl-4                                                          263 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.3 -4                                                            --C.sub.6 H.sub.3                                                              CH.sub.3 -3-Cl-6                                                                264 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F.sub.2 -2,6                                                           C.sub.6 H.sub.3 F.sub.2                                                        -2,6                           265 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OC.sub.6 H.sub.5                                                         -4 --C.sub.6 H.sub.5                                                            266 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 OC.sub.6                                                               H.sub.5 -4 --C.sub.6                                                           H.sub.4 CH.sub.3 -4                                                             267 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H C.sub.6                                                           H.sub.4 CH.sub.2                                                               CH.sub.2 CH.sub.2                                                              --C.sub.6 H.sub.5                                                                    CH.sub.3 -4                                                               268 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H C.sub.6                                                           H.sub.4 CH.sub.2                                                               CH.sub.2 CH.sub.2                                                              --C.sub.6 H.sub.4 Cl-4                                                               CH.sub.3 -4                                                               269 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH(CH.sub.3).sub                                                       .2 -4 --C.sub.6 H.sub.5        270 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 CH(CH.sub.3).sub.2                                                         -4 --C.sub.6 H.sub.4                                                           CH.sub.3 -3                    271 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OH-4 --C.sub.6                                                           H.sub.5                        272 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CN-4 --C.sub.6                                                           H.sub.5                        273 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CN-4 --C.sub.6                                                           H.sub.4 CH.sub.3 -3                                                             274 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 CH.sub.3                                                               -2-Cl-4 --C.sub.6                                                              H.sub.5                        275 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.4                                                           OCF.sub.3 -4                   276 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 F.sub.5                                                        -2,3,4,5,6                     277 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 F5-2,3,4,5,6 --C.sub.6                                                           H.sub.5                        278 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CN-4 --C.sub.6                                                           H.sub.3 Cl.sub.2 -3,4                                                           279 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 CH.sub.3                                                               -2-Cl-4 --C.sub.6                                                              H.sub.4 CH.sub.3 -3                                                             280 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CF.sub.3 -4                                                            --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           281 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 CH.sub.3                                                               -2-Cl-4 --C.sub.6                                                              H.sub.3 (CH.sub.3).sub.2                                                        -3,5                          282 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        CH═CH.sub.2 -3                                                              283 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2                                                               CH.sub.3 -4 --C.sub.6                                                          H.sub.4 CH═CH.sub.2                                                        -3                             284 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CF.sub.3 -4                                                              --C.sub.6 H.sub.4                                                              CH═CH.sub.2 -3                                                              285 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 OH-4 --C.sub.6                                                         H.sub.4 CH.sub.3 -3                                                             286 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H C.sub.6                                                           H.sub.4 OCH.sub.2                                                              CH═CH.sub.2 -4                                                             --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    287 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 CH.sub.2 CH.sub.2                                                          CH.sub.3 -4 --C.sub.6                                                          H.sub.3 Cl.sub.2 -3,4                                                           288 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H C.sub.6                                                           H.sub.4 CH.sub.2                                                               CH.sub.2 CH.sub.3 -4                                                           --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    289 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH═CH.sub.2                                                          -4 C.sub.6 H.sub.4                                                             CH═CH.sub.2 -4                                                              290 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH═CH.sub.2                                                        -4 --C.sub.6 H.sub.4                                                           CH.sub.3 -3                    291 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F.sub.2 -2,6                                                             --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,4                  292 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F.sub.2 -2,6                                                             --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    293 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 Cl-2                                                            --C.sub.6 H.sub.4 Cl-4                                                          294 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H C.sub.6                                                           H.sub.4 CH.sub.2                                                               N(CH.sub.2 CH.sub.3).sub                                                       .2 -2 --C.sub.6 H.sub.4                                                        Cl-4                            - 295 C(O) C(O)                                                                                                                 H --C.sub.6 H.sub.5                                                          --C.sub.6 H.sub.5                                                                - 296 C(O) C(O)                                                              --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.4 Cl-4                                                         --C.sub.6 H.sub.4 Br-2                                                           - 297 C(O) C(O)                                                                H --C.sub.6 H.sub.4                                                          CH.sub.3 -3 --C.sub.6                                                          H.sub.4 CH.sub.3 -3                                                              - 298 C(O) C(O)                                                                H --C.sub.6 H.sub.4                                                          Br-2 --C.sub.6 H.sub.4                                                         Br-2                            - 299 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 --C.sub.6                                                        H.sub.3 (CH.sub.3).sub.2                                                        -3,5                          300 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCH.sub.3 -3                                                             --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           301 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-4 --C.sub.6                                                         H.sub.4 F-4                    302 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.3                                                           (CH.sub.3).sub.2 -3,5                                                           303 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH═CH.sub.2                                                        -4 --C.sub.6 H.sub.3                                                           (CH.sub.3).sub.2 -3,5                                                           304 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H C.sub.6                                                           H.sub.4 (OC(O)CH.sub.3)-                                                       4 --C.sub.6 H.sub.3                                                            (CH.sub.3).sub.2 -3,5                                                           305 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -3,5 --C.sub.6 H.sub.5        306 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -3,5 --C.sub.6 H.sub.4                                                         CH.sub.3 -3                    307 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -3,5 --C.sub.6 H.sub.4                                                         CH.sub.2 CH.sub.3 -4                                                            308 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H C.sub.6                                                           H.sub.4 CH═CHCH.sub.                                                       3 -4 --C.sub.6 H.sub.4                                                         CH═CHCH.sub.3 -4                                                            309 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH(CH.sub.3).sub                                                       .2 -4 --C.sub.6 H.sub.3                                                        (CH.sub.3).sub.2 -3,5                                                           310 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2                                                               CH.sub.3 -4 --C.sub.6                                                          H.sub.4 Br-2                   311 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl-3-CH.sub.3 -4                                                         --C.sub.6 H.sub.5                                                               312 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl-3-CH.sub.3                                                          -4 --C.sub.6 H.sub.4                                                           CH.sub.3 -3                    313 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl-3-CH.sub.3 -4                                                         --C.sub.6 H.sub.4 Cl-4                                                          314 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl-3-CH.sub.3                                                          -4 --C.sub.6 H.sub.3                                                           Cl.sub.2 -3,4                  315 C(O) C(O) C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3 H --C.sub.6 H.sub.4                                                          CH.sub.2 CH.sub.3 -4                                                           --C.sub.6 H.sub.4                                                              NO.sub.2 -2                    316 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F.sub.2 -2,6                                                             --C.sub.6 H.sub.4 Cl-2                                                          317 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F.sub.2 -2,6                                                           --C.sub.6 H.sub.4 Cl-3                                                          318 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F.sub.2 -2,6                                                           --C.sub.6 H.sub.4 Cl-4                                                          319 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F.sub.2 -2,6                                                           --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           320 C(O) C(O) C(CH.sub.                                                       3).sub.2 CH.sub.2                                                              CH.sub.3 H --C.sub.6                                                           H.sub.4 CH.sub.2                                                               CH.sub.3 -4 --C.sub.6                                                          H.sub.3 (CH.sub.3).sub.2                                                        -3,5                          321 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CF.sub.3 -3                                                              --C.sub.6 H.sub.4 Cl-4                                                          322 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CF.sub.3 -3                                                            --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           323 C(S) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.4 Cl-4                   324 C(S) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        CH.sub.3 -3                    325 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 NO.sub.2 -2-                                                             --C.sub.6 H.sub.4                                                              CH.sub.3 -3                         OCH.sub.3 -3                                                              326 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Br-3-CH.sub.3 -4                                                         --C.sub.6 H.sub.5                                                               327 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-4 --C.sub.6                                                         H.sub.4 CO.sub.2                                                               CH.sub.3 -4                    328 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 C.sub.6 H.sub.4                                                             CO.sub.2 Cl#34                 329 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        NH.sub.2 --3                   330 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        NH.sub.2 --2                   331 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 F-4 --C.sub.6                                                            H.sub.5                         - 332 C(O) C(O)                                                                                                                 H --C.sub.6 H.sub.4                                                          CH.sub.3 -4 --C.sub.6                                                          H.sub.4 NO.sub.2 -2                                                              - 333 C(O) C(O)                                                              --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.4 OH-3                                                         --C.sub.6 H.sub.5                                                               334 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2                                                               CH.sub.3 -4 --C.sub.6                                                          H.sub.3 Cl.sub.2 -3,5                                                           335 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H C.sub.6                                                           H.sub.4 OCH.sub.2                                                              CH═CH.sub.2 -3                                                             --C.sub.6 H.sub.5                                                                - 336 C(O) C(O)                                                                H --C.sub.6 H.sub.4                                                          CH.sub.3 -4 --C.sub.6                                                          H.sub.3 (CH.sub.3).sub.2                                                        -3,5                           - 337 C(O) C(O)                                                                                                                 H --C.sub.6 H.sub.4                                                          CH.sub.3 -4 --C.sub.6                                                          H.sub.3 NO.sub.2                                                               -2-CH.sub.3 -3                  - 338 C(O) C(O)                                                                                                                 H --C.sub.6 H.sub.4                                                          CH.sub.3 -4 --C.sub.6                                                          H.sub.3 NO.sub.2                                                               -2-CH.sub.3 -5                  - 339 C(O) C(O)                                                                                                                 H --C.sub.6 H.sub.4                                                          CH.sub.3 -4 --C.sub.6                                                          H.sub.4 CH.sub.3 -3                                                              - 340 C(O) C(O)                                                                H --C.sub.6 H.sub.4                                                          CH.sub.3 -4 --C.sub.6                                                          H.sub.4 I-2                     - 341 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 --C.sub.6                                                        H.sub.4 F-2                    342 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.3                                                           Cl.sub.2 -3,4                  343 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.4                                                           F-2                            344 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 OC(O) N(CH.sub.3).su                                                       b.2 -3 --C.sub.6                                                               H.sub.5                        345 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 CCO.sub.2 CH═CH.                                                       sub.2 -3 --C.sub.6                                                             H.sub.5                        346 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CO.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.4                                                           Cl-4                           347 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CO.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.3                                                           (CH.sub.3).sub.2 -3,5                                                           348 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CO.sub.2                                                               CH.sub.3 -4 --C.sub.6                                                          H.sub.4 CH.sub.3 -3                                                             349 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CO.sub.2                                                               H.sub.4 --C.sub.6                                                              H.sub.4 CH.sub.3 -3                                                             350 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 NH.sub.2 -2-                                                           --C.sub.6 H.sub.4                                                              CH.sub.3 -3                         OCH.sub.3 -3                                                              351 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 NH.sub.2 -4                                                              --C.sub.6 H.sub.4 Cl-4                                                          352 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 NHCO.sub.2                                                             CH.sub.3 -4 --C.sub.6                                                          H.sub.4 Cl-4                   353 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 NHC(O)CH.sub.3 -4                                                        --C.sub.6 H.sub.4 Cl-4                                                          354 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 NHC(O)CH.sub.3                                                         - --C.sub.6 H.sub.4                                                            CH.sub.3 -3                         2-OCH.sub.3 -3                                                            355 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OC.sub.6 H.sub.5                                                         -3 --C.sub.6 H.sub.5                                                            356 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 OC.sub.6                                                               H.sub.5 -3 --C.sub.6                                                           H.sub.4 CH.sub.3 -3                                                             357 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 C(O)CH.sub.3 -4                                                        --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    358 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCH.sub.2                                                                OCH.sub.3 -4 --C.sub.6                                                         H.sub.5                        359 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 OC(O)N(CH.sub.3).sub                                                       .2 -4 --C.sub.6 H.sub.5        360 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 OCH.sub.2 CO.sub.2                                                         CH.sub.3 -4 --C.sub.6                                                          H.sub.5                        361 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 CH.sub.2 OC(O)CH.sub                                                       .3 -4 --C.sub.6 H.sub.5        362 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 SCN-4                                                           --C.sub.6 H.sub.5                                                               363 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2 OH-4                                                          --C.sub.6 H.sub.5                                                               364 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Br-4 --C.sub.6                                                         H.sub.4 Br-4                   365 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCH.sub.2                                                                SCH.sub.3 -4 --C.sub.6                                                         H.sub.5                        366 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 OCH.sub.2 C(CH.sub.3                                                       ).sub.2 -4 --C.sub.6                                                           H.sub.5                        367 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CN-4                                                            --C.sub.6 H.sub.5                                                                - 368 C(O) C(O)                                                              --C(CH.sub.3).sub.3 H                                                            --C.sub.6 H.sub.5                                                              - 369 C(O) C(O)                                                              --C(CH.sub.3).sub.3 H                                                          C.sub.6 H.sub.4                                                                C(CH.sub.3)═NNH                                                            --C.sub.6 H.sub.4                                                              CH.sub.3 -3                         C(O)NH.sub.2 -4                                                           370 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 C.sub.6 H.sub.5                                                          -4 --C.sub.6 H.sub.4                                                           CH.sub.3 -3                    371 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CN-3 --C.sub.6                                                           H.sub.4 CH.sub.3 -3                                                             372 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 NH.sub.2 -3                                                            --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    373 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 C(O)NHC(CH --C.sub.6                                                        H.sub.4 CH.sub.3 -3                                                                 .sub.3).sub.2                                                            CH.sub.2 OH-4                  374 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 CH(OH)CH.sub.3 -4                                                          --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    375 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 NHC(O)C(CH --C.sub.6                                                        H.sub.4 CH.sub.3 -3                                                                 .sub.3)═CH.sub                                                       .2 -3                          376 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CO.sub.2 H-3                                                             --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    377 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 Cl-3                                                            --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    378 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.3                                                           (CH.sub.3).sub.2 -2,3                                                           379 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 --C.sub.6 H.sub.4                                                        CH.sub.3 -3                    380 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        (CH.sub.3).sub.2 -2,3                                                           381 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.3 -4                                                            --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -2,3                                                            - 382 C(O) C(O)                                                                H --C.sub.6 H.sub.4                                                          CH.sub.3 -4 --C.sub.6                                                          H.sub.4 CH.sub.3 -2                                                              - 383 C(O) C(O)                                                                H --C.sub.6 H.sub.4                                                          CH.sub.3 -4 --C.sub.6                                                          H.sub.4 CF.sub.3 -2                                                              - 384 C(O) C(O)                                                                H --C.sub.6 H.sub.4                                                          CH.sub.3 -4 --C.sub.6                                                          H.sub.5                         - 385 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 OCH.sub.2                                                             OCH.sub.3 -4 --C.sub.6                                                         H.sub.4 CH.sub.3 -3                                                             386 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 C(CH.sub.3)═                                                       CH.sub.2 -4 --C.sub.6                                                          H.sub.4 CH.sub.3 -3                                                             387 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 1-naphthyl                                                              388 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 1-naphthyl                                                        --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    389 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 NCS-4 --C.sub.6                                                          H.sub.4 CH.sub.3 -3                                                             390 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -3,5 --C.sub.6 H.sub.3                                                        (CH.sub.3).sub.2 -3,5                                                           391 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl.sub.2 -2,4                                                          --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  392 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 F-2 --C.sub.6                                                            H.sub.4 Br-2                   393 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 F-2 --C.sub.6                                                            H.sub.4 CH.sub.3 -3                                                             394 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 --C.sub.6 H.sub.3                                                        (CH.sub.3).sub.2 -2,3                                                           395 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 F-2 --C.sub.6                                                          H.sub.4 NO.sub.2 -2                                                             396 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 F-2 --C.sub.6                                                          H.sub.5                        397 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 CH.sub.3 -2-Cl-3                                                         --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    398 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 CH.sub.3 -2-Cl-3                                                         --C.sub.6 H.sub.5                                                               399 C(O) C(O) CH(CH.sub                                                       .3)CH.sub.2 C H                                                                --C.sub.6 H.sub.4                                                              CH.sub.3 -4 --C.sub.6                                                          H.sub.3 (CH.sub.3).sub.2                                                        -3,5                             (CH.sub.3).sub.3                                                            400 C(O) C(O) CH(CH.sub.3)CH.sub.2 C H --C.sub.6 H.sub.4 CH.sub.3 -4                                                           --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,4                     (CH.sub.3).sub.3                                                            401 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Br-4 --C.sub.6                                                           H.sub.5                        402 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl.sub.2 -2,3                                                            --C.sub.6 H.sub.4 Br-2                                                          403 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl.sub.2 -2,3                                                          --C.sub.6 H.sub.5                                                               404 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 F-2 --C.sub.6                                                          H.sub.3 (CH.sub.3).sub.2                                                        -3,5                          405 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl.sub.2 -2,3                                                            --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    406 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 2-naphthyl                                                                407 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-naphthyl                                                        --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    408 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        CCF.sub.3 -3                   409 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 NCS-4 --C.sub.6                                                          H.sub.5                        410 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F.sub.2 -2,6                                                             --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  411 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F.sub.2 -2,6                                                             --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,5                  412 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                              --C.sub.6 H.sub.3                                                              (CF.sub.3).sub.2 -3,5                                                           413 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.3 (CF.sub.3).sub.2                                                        -3,5                          414 C(O) C(O) CH(CH.sub.3)C(CH H --C.sub.6 H.sub.4 CH.sub.3 -4 --C.sub.6                                                        H.sub.5                          .sub.3)(CH.sub.2 CH.sub.3).sub.2                                            415 C(O) C(O) CH(CH.sub.3)C(CH H --C.sub.6 H.sub.4 CH.sub.3 -4 --C.sub.6                                                        H.sub.3 (CH.sub.3).sub.                                                       2 -3,5                            .sub.3)(CH.sub.2 CH.sub.3).sub.2                                            416 C(O) C(O) CH(CH.sub.3)C(CH H --C.sub.6 H.sub.4 CH.sub.3 -4 --C.sub.6                                                        H.sub.4 NO.sub.2 -2                                                               .sub.3)(CH.sub.2                                                           CH.sub.3).sub.2                                                                  - 417 C(O) C(O)                                                                H --C.sub.6 H.sub.4                                                          CH.sub.2 CH.sub.3 -4                                                           --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                            - 418 C(O) C(O)                                                                H --C.sub.6 H.sub.4                                                          CH.sub.2 CH.sub.3 -4                                                           --C.sub.6 H.sub.3                                                              NO.sub.2 -2-CH.sub.3 -5         - 419 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                             H.sub.3 Cl-3-F-4                                                                420 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-4 --C.sub.6                                                         H.sub.3 Cl-3-F-4                                                                421 C(O) C(O) --CH(CH.s                                                       ub.3).sub.2 H --C.sub.6                                                        H.sub.4 CH.sub.2                                                               CH.sub.3 -4 --C.sub.6                                                          H.sub.3 (CH.sub.3).sub.2                                                        -3,5                          422 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 --C.sub.6                                                           H.sub.3 (CF.sub.3).sub.2                                                        -3,5                          423 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.3                                                         Cl.sub.2 -314                  424 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                              --C.sub.6 H.sub.3                                                              CH.sub.3 -2-Cl-3                                                                425 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl-3-F-4                                                               --C.sub.6 H.sub.5                                                               426 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H C.sub.6                                                           H.sub.3 (CH.sub.3).sub.2                                                        -2,6 --C.sub.6 H.sub.4                                                        CH.sub.3 -3                    427 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,6 --C.sub.6 H.sub.3                                                         (CH.sub.3).sub.2 -3,5                                                           428 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 --C.sub.6 H.sub.4                                                        Br-2                           429 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.3                                                         (CH.sub.3)2-3,5                                                                 430 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3)2-2,3                                                        --C.sub.6 H.sub.4 Cl-3                                                          431 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 OCF.sub.3 -3                                                           --C.sub.6 H.sub.5                                                               432 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CCF.sub.3 -3                                                           --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    433 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.3                                                         CH.sub.3 -2-Cl-3                                                                 - 434 C(O) C(O)                                                                H --C.sub.6 H.sub.4                                                          CH.sub.2 CH.sub.3 -4                                                           --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                   - 435 C(O) C(O) CH(CH.sub.3)C(CH H --C.sub.6 H.sub.4 CH.sub.3 -4                                                              --C.sub.6 H.sub.3                                                              NO.sub.2 -2-CH.sub.3 -5           .sub.3)(CH.sub.2 CH.sub.3).sub.2                                            436 C(O) C(O) CH(CH.sub.3)C(CH H --C.sub.6 H.sub.4 CH.sub.3 -4 --C.sub.6                                                        H.sub.3 NO.sub.2                                                              -2-CH.sub.3 -3                    .sub.3)(CH.sub.2 CH.sub.3).sub.2                                            437 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F.sub.2 -2,6                                                             --C.sub.6 H.sub.4 Br-2                                                          438 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 CH.sub.3                                                               -2-Cl-3 --C.sub.6                                                              H.sub.3 (CH.sub.3).sub.2                                                        -3,5                          439 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 CH.sub.3 -2-Cl-3                                                         --C.sub.6 H.sub.3                                                              Cl-3-F-4                       440 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.3                                                         Cl-3-F-4                       441 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.3                                                           Cl-3-F-4                       442 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -3,4 --C.sub.6 H.sub.5                                                          443 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -3,4 --C.sub.6 H.sub.4                                                        CH.sub.3 -3                    444 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -314 --C.sub.6 H.sub.4                                                         Cl-2                           445 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -3,4 --C.sub.6 H.sub.3                                                         Cl.sub.2 -2,4                  446 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -3,4 --C.sub.6 H.sub.4                                                         Br-2                           447 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -3,4 --C.sub.6 H.sub.3                                                         (CH.sub.3).sub.2 -3,5                                                           448 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -3,4 --C.sub.6 H.sub.4                                                        NO.sub.2 -2                    449 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -3,4 --C.sub.6 H.sub.3                                                         (CH.sub.3).sub.2 -3,4                                                           450 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.3 (CH.sub.3).sub.2                                                        -3,4                          451 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.3                                                           (CH.sub.3).sub.2 -3,4                                                           452 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F-2-Cl-6                                                               --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    453 C(O) C(O) CH(CH.sub.2 CH.sub.3)C H --C.sub.6 H.sub.4 CH.sub.3 -4                                                           --C.sub.6 H.sub.5                                                                  (CH.sub.3).sub.3                                                            454 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2 Cl-4                                                          --C.sub.6 H.sub.5                                                               455 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (OCH.sub.3).sub.                                                       2 -2,3 --C.sub.6                                                               H.sub.5                        456 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (OCH.sub.3).sub.2                                                        -2,3 --C.sub.6 H.sub.4                                                         Cl-4                           457 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (OCH.sub.3).sub.2                                                        -2,3 --C.sub.6 H.sub.4                                                         Br-2                           458 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl-3-F-4 --C.sub.6                                                        H.sub.3 Cl.sub.2 -3,4                                                          459 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 C(CH.sub.3).sub.                                                       3 -4 --C.sub.6 H.sub.3                                                         (CH.sub.3).sub.2 -3,4                                                           460 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 C(CH.sub.3).sub.                                                       3 -4 --C.sub.6 H.sub.3                                                         (CH.sub.3).sub.2 -3,5                                                           461 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 C(CH.sub.3).sub.                                                       3 -4 --C.sub.6 H.sub.3                                                         Cl.sub.2 -2,4                  462 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 C(CH.sub.3).sub.3                                                        -4 --C.sub.6 H.sub.4                                                           NO.sub.2 -2                    463 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 C(CH.sub.3).sub.3                                                        -4 --C.sub.6 H.sub.4                                                           Br-2                           464 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 C(CH.sub.3).sub.3                                                        -4 --C.sub.6 H.sub.4                                                           CH.sub.3 -3                    465 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 C(CH.sub.3).sub.3                                                        -4 --C.sub.6 H.sub.4                                                           Cl-2                           466 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 C(CH.sub.3).sub.3                                                        -4 --C.sub.6 H.sub.3                                                           Cl.sub.2 -3,4                  467 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -3,4 --C.sub.6 H.sub.3                                                         Cl.sub.2 -3,4                  468 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -3,4 --C.sub.6 H.sub.4                                                         F-4                            469 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 C(CH.sub.3).sub.3                                                        -4 --C.sub.6 H.sub.4                                                           F-4                            470 C(O) C(O) CH(CH.sub.2 CH.sub.3)C H --C.sub.6 H.sub.4 CH.sub.3 -4                                                           --C.sub.6 H.sub.4                                                              NO.sub.2 -2                       (CH.sub.3).sub.3                                                            471 C(O) C(O) CH(CH.sub.2 CH.sub.3)C H --C.sub.6 H.sub.4 CH.sub.3 -4                                                           --C.sub.6 H.sub.3                                                              NO.sub.2 -2-CH.sub.3 -5           (CH.sub.3).sub.3                                                            472 C(O) C(O) CH(CH.sub.2 CH.sub.3)C H --C.sub.6 H.sub.4 CH.sub.3 -4                                                           --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                              (CH.sub.3).sub.3                                                            473 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 NH.sub.2 -2-                                                           --C.sub.6 H.sub.5                                                                  OCH.sub.3 -3                                                                474 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 1-naphthyl                                                        --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  475 C(O) C(O) --C(CH.sub.3).sub.3 H 1-naphthyl --C.sub.6 H.sub.4 Br-2                                                           476 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 CH.sub.3                                                               -2-NO.sub.2 -3 --C.sub.6                                                        H.sub.5                       477 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 CH.sub.3 -2-NO.sub                                                       .2 -3 --C.sub.6 H.sub.4                                                        CH.sub.3 -3                    478 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 CH.sub.3 -2-NO.sub                                                       .2 -3 --C.sub.6 H.sub.4                                                        Cl-4                           479 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 CH.sub.3 -2-NO.sub                                                       .2 -3 --C.sub.6 H.sub.3                                                        Cl.sub.2 -2,4                  480 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 CH.sub.3 -2-Br-3                                                         --C.sub.6 H.sub.5                                                               481 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 CH.sub.3                                                               -2-Br-3 --C.sub.6                                                              H.sub.4 CH.sub.3 -3                                                             482 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 CH.sub.3                                                               -2-Br-3 --C.sub.6                                                              H.sub.4 Cl-4                   483 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 CH.sub.3 -2-Br-3                                                         --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  484 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 CH.sub.3 -2-NH.sub                                                       .2 -3 --C.sub.6 H.sub.4                                                        CH.sub.3 -3                    485 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -2                                                              --C.sub.6 H.sub.4 Br-2                                                          486 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.3 -2                                                            --C.sub.6 H.sub.4                                                              NO.sub.2 -2                    487 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -2                                                              --C.sub.6 H.sub.4 Cl-3                                                          488 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.3 -2                                                            --C.sub.6 H.sub.4 Cl-4                                                          489 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.3 -2                                                            --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    490 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -2                                                              --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           491 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.3 -2                                                            --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,4                  492 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -2                                                              --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,5                  493 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 CH.sub.3 -2-F-3                                                          --C.sub.6 H.sub.5                                                               494 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 CH.sub.3 -2-F-3                                                        --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    495 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F-2-Cl-6 --C.sub.6                                                        H.sub.5                       496 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F-2-Cl-6 --C.sub.6                                                        H.sub.3 Cl.sub.2 -2,4                                                          497 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F-2-Cl-6                                                               --C.sub.6 H.sub.4 F-4                                                           498 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2                                                               CH.sub.2 Cl-4 --C.sub.6                                                        H.sub.3 (CH.sub.3).sub.2                                                        -3,5                          499 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.2 F.sub.3 -2,4,6                                                           --C.sub.6 H.sub.5                                                               500 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.2 F.sub.3 -2,4,6                                                         --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  501 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.2 F.sub.3 -2,4,6                                                           --C.sub.6 H.sub.4 Br-2                                                          502 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.2 F.sub.3 -2,4,6                                                         --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           503 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 NO.sub.2                                                               -2-Cl-3 --C.sub.6                                                              H.sub.5                        504 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 NO.sub.2 -2-Cl-3                                                         --C.sub.6 H.sub.4 Br-2                                                          505 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 NO.sub.2                                                               -2-Cl-3 --C.sub.6                                                              H.sub.4 NO.sub.2 -2                                                             506 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 NO.sub.2                                                               -2-Cl-3 --C.sub.6                                                              H.sub.4 CH.sub.3 -3                                                             507 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 NO.sub.2                                                               -2-Cl-3 --C.sub.6                                                              H.sub.4 Cl-3                   508 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 NO.sub.2 -2-Cl-3                                                         --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  509 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 NO.sub.2 -2-Cl-3                                                         --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,5                  510 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 NO.sub.2 -2-Cl-3                                                         --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           511 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2                                                               CH.sub.3 -4 --C.sub.6                                                          H.sub.3 F.sub.2 -2,3                                                            512 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2                                                               CH.sub.3 -4 --C.sub.6                                                          H.sub.3 Cl.sub.2 -2,3                                                           513 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F.sub.2 -2,3                                                           --C.sub.6 H.sub.5                                                               514 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl.sub.2 -2,3                                                          --C.sub.6 H.sub.4                                                              NO.sub.2 -2                    515 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        F.sub.2 -2,3                   516 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl.sub.2 -2,3                                                            --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           517 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl.sub.2 -2,3                                                          --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  518 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl.sub.2 -2,3                                                            --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,5                  519 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl.sub.2 -2,3                                                            --C.sub.6 H.sub.4 Cl-3                                                          520 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl.sub.2 -2,3                                                          C.sub.6 H.sub.3                                                                (CH.sub.3).sub.2 -2,3                                                           521 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F.sub.2 -2,3                                                           --C.sub.6 H.sub.4 Br-2                                                          522 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 --C.sub.6 H.sub.4                                                        Cl-4                           523 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 C.sub.6 H.sub.3                                                           Cl.sub.2 -2,4                  524 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.3                                                         F.sub.2 -2,6                   525 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.3                                                         F.sub.2 -2,4                   526 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.4                                                         OCH.sub.3 -3                   527 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.4                                                         OCH.sub.3 -2                   528 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.4                                                         CH.sub.3 -2                    529 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.4                                                         CH.sub.3 -4                    530 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 CH.sub.3 -2-Cl-3                                                         --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  531 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.2                                                        Cl-4 --C.sub.6 H.sub.5                                                          532 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2                                                               CH.sub.2 Cl-4 --C.sub.6                                                        H.sub.3 Cl.sub.2 -2,4                                                           533 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F-3-CH.sub.3 -4                                                        --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           534 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F-3-CH.sub.3 -4                                                        --C.sub.6 H.sub.3                                                              F.sub.2 -3,5                   535 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 F-3-CH.sub.3 -4                                                          --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    536 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F-3-CH.sub.3 -4                                                          --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,5                  537 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F-3-CH.sub.3 -4                                                          --C.sub.6 H.sub.4                                                              NO.sub.2 -2                    538 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F-3-CH.sub.3 -4                                                          --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  539 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.3                                                           F.sub.2 -3,5                   540 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.4                                                         I-2                            541 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.2                                                        OH-4 --C.sub.6 H.sub.3                                                         (CH.sub.3).sub.2 -3,5                                                           542 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.2 F.sub.2                                                                -2,6--CH.sub.3 -3                                                              --C.sub.6 H.sub.5                                                               543 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.2 F.sub.2                                                                -2,6--CH.sub.3 -3                                                              --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    544 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.2 F.sub.2 -2,6--CH.s                                                       ub.3 -3 --C.sub.6                                                              H.sub.3 Cl.sub.2 -2,4                                                           545 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-4 --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3                           - 546 C(O) C(O)                                                                                                                 H --C.sub.6 H.sub.3                                                          (CH.sub.3).sub.2 -2,3                                                          --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                            - 547 C(O) C(O)                                                                H --C.sub.6 H.sub.3                                                          (CH.sub.3).sub.2 -2,3                                                          --C.sub.6 H.sub.4                                                              CH.sub.3 -3                     - 548 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F-2-Cl-6                                                              --C.sub.6 H.sub.3                                                              F.sub.2 -2,3                   549 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.3 F.sub.2 -2,3                                                               --C.sub.6 H.sub.4                                                              NO.sub.2 -2                    550 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F.sub.2 -2,3                                                             --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    551 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F.sub.2 -2,3                                                             --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           552 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F.sub.2 -2,3                                                           --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  553 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.3                                                         F.sub.2 -2,3                   554 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.3                                                         Cl.sub.2 -2,3                  555 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.3                                                         (CH.sub.3).sub.2 -3,4                                                           556 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -213 --C.sub.6 H.sub.4                                                        NO.sub.2 -2                    557 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.3                                                           CH.sub.3 -2-Cl-5                                                                558 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 --C.sub.6 H.sub.5        559 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        CH.sub.3 -2-Cl-5                                                                560 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F.sub.2 -2,6                                                           --C.sub.6 H.sub.3                                                              CH.sub.3 -2-Cl-5                                                                561 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 --C.sub.6 H.sub.3                                                        CH.sub.3 -2-Cl-5                                                                562 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 CH.sub.3                                                               -2-Cl-3 --C.sub.6                                                              H.sub.3 CH.sub.3                                                               -2-Cl-5                        563 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F.sub.2 -2,6                                                             --C.sub.6 H.sub.3                                                              Cl-2-CH.sub.3 -5                                                                564 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 --C.sub.6 H.sub.3                                                        Cl-2-CH.sub.3 -5                                                                565 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 CH.sub.3                                                               -2-Cl-3 --C.sub.6                                                              H.sub.3 Cl-2-CH.sub.3                                                          -5                             566 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 --C.sub.6                                                           H.sub.3 CH.sub.3                                                               -2-Cl-5                        567 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 --C.sub.6                                                           H.sub.3 Cl-2-CH.sub.3                                                          -5                             568 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F-2-Cl-4 --C.sub.6                                                        H.sub.5                       569 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F-2-Cl-4 --C.sub.6                                                        H.sub.4 CH.sub.3 -3                                                            570 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F-2-Cl-4                                                               --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           571 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F-2-Cl-4                                                               --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,5                  572 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F-2-Cl-4 --C.sub.6                                                        H.sub.4 Br-2                  573 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F-2-Cl-4 --C.sub.6                                                        H.sub.4 NO.sub.2 -2                                                            574 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl-2-CH.sub.3                                                          -3 C.sub.6 H.sub.3                                                             Cl.sub.2 -2,4                  575 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl-2-CH.sub.3 -3                                                         --C.sub.6 H.sub.5                                                               576 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl-2-CH.sub.3                                                          -3 --C.sub.6 H.sub.4                                                           CH.sub.3 -3                    577 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl-2-CH.sub.3 -3                                                         --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           578 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl-2-CH.sub.3                                                          -3 --C.sub.6 H.sub.3                                                           Cl.sub.2 -3,5                  579 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Br-2-CH.sub.3 -3                                                         --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           580 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Br-2-CH.sub.3                                                          -3 --C.sub.6 H.sub.3                                                           Cl.sub.2 -2,4                  581 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Br-2-CH.sub.3 -3                                                         --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    582 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Br-2-CH.sub.3 -3                                                         --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,5                  583 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Br-2-CH.sub.3 -3                                                         --C.sub.6 H.sub.4 Br-2                                                          584 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 --C.sub.6 H.sub.4                                                        Cl-2                           585 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.4                                                         CF.sub.3 -2                    586 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.4                                                         CH.sub.2 CH.sub.3 -                                                             587 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 --C.sub.6 H.sub.3                                                        Cl.sub.2 -3,5                  588 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F.sub.2 -2,6                                                             --C.sub.6 H.sub.3                                                              Cl-3-F-4                       589 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 --C.sub.6                                                           H.sub.3 F.sub.2 -3,5                                                            590 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 --C.sub.6 H.sub.3                                                        F.sub.2 -3,5                   591 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 CH.sub.3 -2-Cl-3                                                         --C.sub.6 H.sub.3                                                              F.sub.2 -3,5                   592 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        F.sub.2 -3,5                   593 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 --C.sub.6 H.sub.3                                                           (CH.sub.3).sub.2 -2,5                                                           594 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F.sub.2 -2,6                                                           --C.sub.6 H.sub.3                                                              F.sub.2 -3,5                   595 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 CH.sub.3 -2-Cl-3                                                         --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,5                  596 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 C.sub.6 H.sub.3                                                           (CH.sub.3).sub.2 -2,5                                                           597 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Br-2 --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -3,5                          598 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Br-2-CH.sub.3 -3                                                         --C.sub.6 H.sub.4 Cl-3                                                          599 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl-2-CH.sub.3                                                          -3 --C.sub.6 H.sub.4                                                           Cl-3                           600 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Br-2-CH.sub.3 -3                                                         --C.sub.6 H.sub.4                                                              NO.sub.2 -2                    601 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl-2-CH.sub.3 -3                                                         --C.sub.6 H.sub.4                                                              NO.sub.2 -2                    602 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.3                                                         NO.sub.2 -2-CH.sub.3 -3        603 C(O) C(O) --C(CH.sub.3).sub.3 H C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                           -2,3 --C.sub.6 H.sub.3                                                         NO.sub.2 -2-CH.sub.3 -5        604 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F.sub.2 -2,6                                                             --C.sub.6 H.sub.5                                                               605 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,6 C.sub.6 H.sub.3                                                          Cl.sub.2 -2,4                  606 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.2 (CH.sub.3).sub.3                                                         -2,4,6 --C.sub.6                                                               H.sub.3 (CH.sub.3).sub.2                                                        -3,5                          607 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.2 (CH.sub.3).sub.3                                                         -2,4,6 --C.sub.6                                                               H.sub.3 Cl.sub.2 -2,4                                                           608 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 F.sub.2 -2,6                                                           --C.sub.6 H.sub.4                                                              CH.sub.3 -4                    609 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F.sub.2 -2,6                                                             --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,5                  610 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.2 (CH.sub.3).sub.3                                                         -2,4,6 --C.sub.6                                                               H.sub.4 Cl-4                   611 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.2 (CH.sub.3).sub.3                                                         -2,4,6 --C.sub.6                                                               H.sub.4 CH.sub.3 -3                                                             612 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.2 (CH.sub.3).sub.3                                                        -2,4,6 --C.sub.6                                                              H.sub.3 Cl.sub.2 -3,4                                                           613 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CC(O)CH.sub.3                                                          -2 --C.sub.6 H.sub.4                                                           OC(O)CH.sub.3 -2                                                                614 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 OH-2 --C.sub.6                                                         H.sub.4 OH-2                   615 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,4 --C.sub.6 H.sub.4                                                         CH.sub.3 -3                    616 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,4 --C.sub.6 H.sub.3                                                         Cl.sub.2 -2,4                  617 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,4 --C.sub.6 H.sub.3                                                         (CH.sub.3).sub.2 -3,5                                                           618 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,4 --C.sub.6 H.sub.3                                                        Cl.sub.2 -3,5                  619 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,4 --C.sub.6 H.sub.4                                                         Br-3                           620 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,4 --C.sub.6 H.sub.3                                                         Cl.sub.2 -3,4                  621 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Br-2-CH.sub.3 -3                                                         --C.sub.6 H.sub.5                                                               622 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 3,4-methyle                                                       nedioxy --C.sub.6                                                              H.sub.5                        623 C(O) C(O) --C(CH.sub.3).sub.3 H 3,4-methylenedioxy --C.sub.6                                                               H.sub.4 Cl-4                   624 C(O) C(O) --C(CH.sub.3).sub.3 H 314-methylenedioxy --C.sub.6                                                               H.sub.4 CH.sub.3 -3                                                             625 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 4-(4,4-dime                                                       thyl-2- --C.sub.6                                                              H.sub.4 CH.sub.3 -3                                                                  oxazinyl)phenyl                                                           626 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-pyrolylph                                                       enyl --C.sub.6 H.sub.5                                                          627 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-pyrolylph                                                       enyl --C.sub.6 H.sub.4                                                         CH.sub.3 -3                    628 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C.sub.6 H.sub.3                                                         Br-2-Cl-5                      629 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 CH.sub.3 -2-Cl-3                                                         --C.sub.6 H.sub.4 Cl-3                                                          630 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 CH.sub.3                                                               -2-Cl-3 --C.sub.6                                                              H.sub.4 F-3                    631 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 CH.sub.3 -2-Cl-3                                                         --C.sub.6 H.sub.4 Br-2                                                          632 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 CH.sub.3                                                               -2-Cl-3 --C.sub.6                                                              H.sub.3 CH.sub.3                                                               -2-Cl-3                        633 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 CH.sub.3 -2-Cl-3                                                         --C.sub.6 H.sub.2                                                              (CH.sub.3).sub.2                                                               -3,5--Cl-4                      - 634 C(O) C(O)                                                                                                                 H --C.sub.6 H.sub.5                                                          --C.sub.6 H.sub.3                                                              CH.sub.3 -2-Cl-3                                                                 - 635 C(O) C(O)                                                              --C(CH.sub.3).sub.3                                                            CH.sub.3 --C.sub.6                                                             H.sub.5 --C.sub.6                                                              H.sub.5                        636 C(O) C(O) --C(CH.sub.3).sub.3 CH.sub.2 --C.sub.6 H.sub.5 --C.sub.6                                                         H.sub.5 --C.sub.6                                                              H.sub.5                        637 C(O) C(O) --C(CH.sub.3).sub.3 CH.sub.2 CH═CH.sub.2 --C.sub.6                                                           H.sub.5 --C.sub.6                                                              H.sub.5                        638 C(O) C(O) --C(CH.sub.3).sub.3 CH.sub.2 OCH.sub.3 --C.sub.6 H.sub.5                                                         --C.sub.6 H.sub.5                                                               639 C(O) C(O) --C(CH.su                                                       b.3).sub.3 --CH.sub.2                                                          SCH.sub.3 --C.sub.6                                                            H.sub.5 --C.sub.6                                                              H.sub.5                        640 C(O) C(O) --C(CH.sub.3).sub.3 --CH.sub.2 C═CH --C.sub.6 H.sub.5                                                        --C.sub.6 H.sub.5                                                               641 C(O) C(O) --C(CH.su                                                       b.3).sub.3 --CH.sub.2                                                          C═CH --C.sub.6                                                             H.sub.4 CH.sub.3 -4                                                            --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    642 C(O) C(O) --C(CH.sub.3).sub.3 --CH.sub.2 C═CH --C.sub.6 H.sub.5                                                        --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           643 C(O) C(O) --C(CH.su                                                       b.3).sub.3 --CH.sub.2                                                          C═CH --C.sub.6                                                             H.sub.5 --C.sub.6                                                              H.sub.3 Cl.sub.2 -2,4                                                           644 C(O) C(O) --C(CH.su                                                       b.3).sub.3 --CH.sub.2                                                          C═CH --C.sub.6                                                             H.sub.5 --C.sub.6                                                              H.sub.3 Cl.sub.2 -3,4                                                           645 C(O) C(O) --C(CH.su                                                       b.3).sub.3 CH.sub.2                                                            C.sub.6 H.sub.4 Br-4                                                           --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.5                                                               646 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.11 --C.sub.6                                                             H.sub.5                        647 C(O) C(O) --C(CH.sub.3).sub.3 H --CH.sub.2 CH.sub.2 CH.sub.3                                                               --C.sub.6 H.sub.4 Cl-4                                                          648 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --CH.sub.2                                                        CH.sub.2 CH.sub.2                                                              CH.sub.3 --C.sub.6                                                             H.sub.5                        649 C(O) C(O) --C(CH.sub.3).sub.3 H --CH.sub.2 CH.sub.2 CH.sub.2                                                               CH.sub.3 --C.sub.6                                                             H.sub.4 Cl-4                   650 C(O) C(O) --C(CH.sub.3).sub.3 H --CH.sub.2 CH.sub.2 CH.sub.2                                                               CH.sub.3 --C.sub.6                                                             H.sub.4 CH.sub.3 -4                                                             651 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --CH.sub.2                                                        CH.sub.2 CH.sub.3                                                              --C.sub.6 H.sub.5                                                               652 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --CH.sub.2                                                        CH.sub.2 CH.sub.2                                                              CH.sub.3 --C.sub.6                                                             H.sub.4 F-4                    653 C(O) C(O) --C(CH.sub.3).sub.3 H --CH.sub.2 CH.sub.2 CH.sub.2                                                               CH.sub.3 --C.sub.6                                                             H.sub.4 CF.sub.3 -4                                                             654 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --CH.sub.2                                                        C.sub.6 H.sub.5                                                                --C.sub.6 H.sub.5                                                               655 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C(CH.sub.                                                       3).sub.3 --C.sub.6                                                             H.sub.4 Cl-4                   656 C(O) C(O) --C(CH.sub.3).sub.3 H cyclohex-1-enyl --C.sub.6 H.sub.5                                                           657 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --CH.sub.2                                                        Cl --C.sub.6 H.sub.5                                                            658 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --CHCl.sub.                                                       2 --C.sub.6 H.sub.5                                                             659 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --CCl.sub.3                                                        --C.sub.6 H.sub.5                                                              660 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C(CH.sub.                                                       3).sub.2 CH.sub.2 Cl                                                           --C.sub.6 H.sub.5                                                               661 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C(Cl).dbd                                                       .CCl.sub.2 --C.sub.6                                                           H.sub.5                        662 C(O) C(O) --C(CH.sub.3).sub.3 H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                        CH.sub.3 --C.sub.6                                                             H.sub.3 Cl.sub.2 -3,4                                                           663 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H CH.sub.2                                                          CH.sub.2 CH.sub.2                                                              CH.sub.2 CH.sub.3                                                              --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    664 C(O) C(O) --C(CH.sub.3).sub.3 H --C(CH.sub.3)═CH.sub.2 --C.sub.6                                                        H.sub.5                       665 C(O) C(O) --C(CH.sub.3).sub.3 H cyclobutanyl --C.sub.6 H.sub.5                                                              666 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-norbornyl                                                        --C.sub.6 H.sub.4                                                             CH.sub.3 -3                    667 C(O) C(O) --C(CH.sub.3).sub.3 H cyclohex-3enyl --C.sub.6 H.sub.4                                                           CH.sub.3 -3                    668 C(O) C(O) --C(CH.sub.3).sub.3 H --CH.sub.2 CO.sub.2 --CH.sub.2                                                             CH.sub.3 --C.sub.6                                                             H.sub.4 Cl.sub.2 -3,4                                                            - 669 C(O) C(O)                                                              --C(CH.sub.3).sub.3 H                                                            --C.sub.6 H.sub.4                                                            Cl.sub.2 -3,4                   - 670 C(O) C(O) --C(CH.sub.3).sub.3 H 3-acetyl-2,2- --C.sub.6 H.sub.4                                                         CH.sub.3 -3                         dimethylcyclobutyl-                                                            methyl                                                                    671 C(O) C(O) --C(CH.sub.3).sub.3 H --CH═CHCH.sub.2 CH.sub.3                                                               --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    672 C(O) C(O) --C(CH.sub.3).sub.3 H --CH.sub.2 CH.sub.2 CH═CH.sub.2                                                        --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    673 C(O) C(O) --C(CH.sub.3).sub.3 H CH.sub.2 CH.sub.2 CH.sub.2 CO.sub.2                                                        CH.sub.3 --C.sub.6                                                             H.sub.4 CH.sub.3 -3                                                             674 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --CH(CH.sub                                                       .3).sub.2 --C.sub.6                                                            H.sub.3 (CH.sub.3).sub.2                                                        -3,5                          675 C(O) C(O) --C(CH.sub.3).sub.3 H 2-propenyl --C.sub.6 H.sub.3                                                               (CH.sub.3).sub.2 -3,5                                                           676 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --CH(CH.sub                                                       .3).sub.2 --C.sub.6                                                            H.sub.4 Br-2                   677 C(O) C(O) --C(CH.sub.3).sub.3 H --CH(CH.sub.3).sub.2 --C.sub.6                                                             H.sub.5                        678 C(O) C(O) --C(CH.sub.3).sub.3 H 3,4-E-dihydroxy --C.sub.6 H.sub.4                                                          CH.sub.3 -3                         cyclohexane                                                               679 C(O) C(O) --C(CH.sub.3).sub.3 H 3,4-Z-dihydroxy --C.sub.6 H.sub.4                                                          CH.sub.3 -3                         cyclohexane                                                               680 C(O) C(O) --C(CH.sub.3).sub.3 H O CH.sub.3 --C.sub.6 H.sub.4                                                               CH.sub.3 -3                    681 C(O) C(O) --C(CH.sub.3).sub.3 H 2-methylcyclohex- --C.sub.6 H.sub.4                                                        CH.sub.3 -3                         2,5-dienyl                                                                682 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 CH.sub.2 CH.sub.2                                                        CH.sub.2 CH.sub.2                                                              CH.sub.3                       683 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 cyclohexenyl                                                              684 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl.sub.2 -3,5                                                          --CH.sub.2 CH.sub.2 Br                                                          685 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl.sub.2 -3,5                                                          --CH.sub.2 Cl                  686 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl.sub.2 -3,5                                                            --CH(CH.sub.3)Br                                                                687 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl.sub.2 -3,5                                                          --CH═CH.sub.2                                                               688 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C(CH.sub.3).su                                                       b.3                            689 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --CH.sub.2                                                               C.sub.6 H.sub.5                                                                 690 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl.sub.2 -3,4                                                          --CH.sub.3                     691 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 2-trifluoromethyl-             1-propenyl                                                               692 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 --C(CH.sub.3)                                                       .sub.3                         693 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 --CH═CHC.                                                       sub.6 H.sub.5                  694 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 --CH.sub.2                                                          C.sub.6 H.sub.5                                                                 695 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 NO.sub.2                                                               -2-Cl-4 --CH═CHC.sub                                                       .6 H.sub.4 CF.sub.3 -3                                                          696 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 NO.sub.2                                                               -2-Cl-4 --CH═CHC.sub                                                       .6 H.sub.4 CN-4                                                                 697 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 NO.sub.2                                                               -2-Cl-4 --CH═CHC.sub                                                       .6 H.sub.4 Cl-4                                                                 698 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 cyclohexenyl                                                            699 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --C(CH.sub.3).db                                                       d.CH.sub.2                     699 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 2-phenylcyclopropy                                                       l                              701 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl.sub.2 -3,4                                                            cyclopropyl                    702 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 cyclobutyl                                                           703 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 2-(3-furyl)ethen                                                       yl                             704 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --CHCO.sub.2                                                             CH.sub.2 CH.sub.3 -                                                                   CH.sub.2 OH                                                              705 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 3-cyclohexenyl                                                            706 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 1-(4-chlorophenyl)                                                       -                                    2-methyl-2-propyl                                                        707 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 2-methylcyclohex-              2,5-dienyl                                                               708 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --CC--C.sub.6                                                            H.sub.5                        709 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --CH(CH.sub.3)CH.s                                                       ub.2 CH.sub.3                  710 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 1-phenyl-2-methyl-             1-butyl                                                                  711 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 3-acetyl-2,2-                                                                   dimethylcyclobuty                                                       l-                                   methyl                                                                   712 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --CH═CHCH.sub.                                                       2 CH.sub.3                     713 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --CH.sub.2                                                               CH.sub.2 CH═CH.sub.2       714 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 CH.sub.2 CH.sub.2                                                        CH.sub.2 CO.sub.2                                                              CH.sub.3                       715 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --CH.sub.2                                                               OCH.sub.3                      716 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 2-propenyl                                                                 717 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2                                                               CH.sub.3 -4 2-propenyl                                                          718 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 --CH(CH.sub.3).sub                                                       .2                             719 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 --C(CH.sub.3).sub.3       720 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 2-but-1-enyl                                                               721 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 2-pent-2-enyl                                                             722 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 4-pyridyl                                                               723 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-pyridyl                                                         C.sub.6 H.sub.5                                                                 724 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 3-pyridyl                                                               725 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 3-pyridyl                                                         --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,4                  726 C(O) C(O) --C(CH.sub.3).sub.3 H 3-pyridyl --C.sub.6 H.sub.5                                                                 727 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-pyridyl                                                         --C.sub.6 H.sub.4                                                              NO.sub.2 -2                    728 C(O) C(O) --C(CH.sub.3).sub.3 H 2-pyridyl --C.sub.6 H.sub.4                                                                CH.sub.2 CH.sub.3 -4                                                            729 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-pyridyl                                                         --C.sub.6 H.sub.4 Br-2                                                          730 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.2                                                               CH.sub.3 -4 2-pyridyl                                                           731 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 OCF.sub.3 -4                                                           2-pyridyl                      732 C(O) C(O) --C(CH.sub.3).sub.3 H 2-pyridyl --C.sub.6 H.sub.4                                                                CH.sub.3 -3                    733 C(O) C(O) --C(CH.sub.3).sub.3 H 2-pyridyl --C.sub.6 H.sub.3                                                                Cl.sub.2 -3,4                  734 C(O) C(O) --C(CH.sub.3).sub.3 H 5-propyl-2-pyridyl --C.sub.6                                                               H.sub.5                        735 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 2-pyrazinyl                                                               736 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-pyridyl                                                         --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           737 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 3-bromo-2-p                                                       yridyl --C.sub.6                                                               H.sub.4 Cl-4                   738 C(O) C(O) --C(CH.sub.3).sub.3 H 2-pyrazinyl --C.sub.6 H.sub.5                                                               739 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 4-pyridyl                                                         --C.sub.6 H.sub.5                                                               740 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-pyridyl                                                         --C.sub.6 H.sub.4                                                              OCH.sub.3 -4                   741 C(O) C(O) --C(CH.sub.3).sub.3 H 2-pyridyl --C.sub.6 H.sub.4 I-2                                                             742 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-pyridyl                                                         --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  743 C(O) C(O) --C(CH.sub.3).sub.3 H 2-pyridyl --C.sub.6 H.sub.4 F-4                                                             744 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-pyridyl                                                         --C.sub.6 H.sub.4                                                              CF.sub.3 -2                    745 C(O) C(O) --C(CH.sub.3).sub.3 H 2-pyridyl --C.sub.6 H.sub.4                                                                NO.sub.2 -3                    746 C(O) C(O) --C(CH.sub.3).sub.3 H 4-pyridyl C.sub.6 H.sub.4 CH.sub.3                                                         -3                             747 C(O) C(O) --C(CH.sub.3).sub.3 H 2-pyridyl --C.sub.6 H.sub.4 Cl-2                                                            748 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-pyridyl                                                         --C.sub.6 H.sub.4                                                              OCH.sub.3 -3                   749 C(O) C(O) --C(CH.sub.3).sub.3 H 2-pyridyl --C.sub.6 H.sub.4 F-4                                                             750 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 2-methanesulfony                                                       l-                                   5-pyridyl                                                                751 C(O) C(O) --C(CH.sub.3).sub.3 H 4-pyrimidinyl --C.sub.6 H.sub.4 F-4        752 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 4-pyrimidinyl                                                             753 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-pyridyl                                                         --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -2,3                                                           754 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 2-pyridyl                                                               755 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 2-pyridyl                                                               756 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H N --C.sub.6                                                        H.sub.4 CH.sub.3 -3                                                            757 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 2-Cl-3-pyridyl                                                            758 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-pyridyl                                                         --C.sub.6 H.sub.3                                                              Cl-2-CH.sub.3 -5                                                                759 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-Cl-3-pyri                                                       dyl --C.sub.6 H.sub.3                                                          Cl-2-CH.sub.3 -5                                                                760 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-thiomethy                                                       l-3- --C.sub.6 H.sub.4                                                         CH.sub.3 -3                         pyridyl                                                                   761 C(O) C(O) --C(CH.sub.3).sub.3 H 2-thiomethyl-3- --C.sub.6 H.sub.3                                                          Cl.sub.2 -3,4                       pyridyl                                                                   762 C(O) C(O) --C(CH.sub.3).sub.3 H 2-Cl-3-pyridyl --C.sub.6 H.sub.5                                                            763 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-pyridyl                                                         --C.sub.6 H.sub.3                                                              Cl-2-F-3                       764 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 2-furyl                  765 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 2-thienyl                                                                 766 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-thienyl                                                         --C.sub.6 H.sub.5                                                               767 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 2-furyl                                                           --C.sub.6 H.sub.5                                                               768 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.3 -3                                                            2-thienyl                      769 C(O) C(O) --C(CH.sub.3).sub.3 H 2-thienyl --C.sub.6 H.sub.5                                                                CH.sub.3 -4                    770 C(O) C(O) --C(CH.sub.3).sub.3 H 2-furyl --C.sub.6 H.sub.4 CH.sub.3                                                         -3                             771 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                              2-furyl                        772 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                              2,5-di-Cl-3-thienyl                                                             773 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 Cl.sub.2 -3,4                                                          2-thienyl                      774 C(O) C(O) --C(CH.sub.3).sub.3 H 3-thienyl --C.sub.6 H.sub.5                                                                 775 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 3-thienyl                                                         --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    776 C(O) C(O) --C(CH.sub.3).sub.3 H 3-thienyl --C.sub.6 H.sub.3                                                                Cl.sub.2 -3,4                  777 C(O) C(O) --C(CH.sub.3).sub.3 H 3-thienyl --C.sub.6 H.sub.4 Cl-4                                                            778 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H N-methyl-2-                                                       pyrolyl --C.sub.6                                                              H.sub.5                        779 C(O) C(O) --C(CH.sub.3).sub.3 H N-methyl-2-pyrolyl --C.sub.6                                                               H.sub.4 Cl-4                   780 C(O) C(O) --C(CH.sub.3).sub.3 H N-methyl-2-pyrolyl --C.sub.6                                                               H.sub.4 CH.sub.3 -3                                                             781 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 3-furyl                                                           --C.sub.6 H.sub.5                                                               782 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 3-furyl                                                           --C.sub.6 H.sub.4                                                              CH.sub.3 -2                    783 C(O) C(O) --C(CH.sub.3).sub.3 H 3-furyl --C.sub.6 H.sub.4 Cl-4                                                              784 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 3-furyl                                                           --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  785 C(O) C(O) --C(CH.sub.3).sub.3 H 3-furyl --C.sub.6 H.sub.4 CH.sub.3                                                         -3                             786 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F.sub.2 -2,6                                                             2-thienyl                      787 C(O) C(O) --C(CH.sub.3).sub.3 H 4-3H-triazolyl --C.sub.6 H.sub.4                                                           CH.sub.3 -3                    788 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl-2-0CH.sub.3 -3                                                        2-furyl                        789 C(O) C(O) --C(CH.sub.3).sub.3 H 3-methyl-2-thienyl --C.sub.6                                                               H.sub.4 CH.sub.3 -3                                                             790 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 3-methyl-2-thien                                                       yl                             791 C(O) C(O) --C(CH.sub.3).sub.3 H 3,5-dimethyl-4- --C.sub.6 H.sub.5                                                                oxazolyl                 792 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.2 CH.sub.3                                                        -4 2-phenyl-4-triazolyl        793 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 4,4-dimethyl-2-                                                                 oxazolyl                                                                 794 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H 3,5-thiomet                                                       hyl-4- --C.sub.6                                                               H.sub.5                             1,2-oxazolyl                                                              795 C(O) C(O) --CH(CH.sub.3)CF.sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.                                                       2 -2,3 --C.sub.6                                                               H.sub.3 Cl.sub.2 -2,4                                                           796 C(O) C(O) --CH(CH.s                                                       ub.3)CF.sub.3 H                                                                --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -2,3                                                          --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           797 C(O) C(O) --CH(CH.s                                                       ub.3)CF.sub.3 H                                                                --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -2,3                                                          --C.sub.6 H.sub.3                                                              NO.sub.2 -2-CH.sub.3 -5        798 C(O) C(O) --CH(CH.sub.3)CF.sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                             H.sub.5                        799 C(O) C(O) --CH.sub.2 CF.sub.3 H --C.sub.6 H.sub.3 Cl.sub.2 -3,4                                                            --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,4                  800 C(O) C(O) --CH.sub.2 CF.sub.3 H --C.sub.6 H.sub.4 Cl-4 --C.sub.6                                                           H.sub.4 Cl-4                   801 C(O) C(O) --CH.sub.2 CF.sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.5        802 C(O) C(O) --C(CH.sub.3).sub.2 CN H --C.sub.6 H.sub.5 --C.sub.6                                                             H.sub.5                        803 C(O) C(O) --C(CH.sub.3).sub.2 CN H --C.sub.6 H.sub.5 --C.sub.6                                                             H.sub.4 Cl-4                   804 C(O) C(O) --C(CH.sub.3).sub.2 CN H --C.sub.6 H.sub.4 CH.sub.3 -4                                                           --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    805 C(O) C(O) --C(CH.sub.3).sub.2 CN H --C.sub.6 H.sub.5 --C.sub.6                                                             H.sub.4 CH.sub.3 -3                                                             806 C(O) C(O) --C(CH.su                                                       b.3).sub.2 CN H                                                                --C.sub.6 H.sub.4 Cl-4                                                         --C.sub.6 H.sub.4 Cl-4                                                          807 C(O) C(O) --C(CH.su                                                       b.3).sub.2 CN H                                                                --C.sub.6 H.sub.4                                                              CH.sub.3 -4 --C.sub.6                                                          H.sub.3 (CH.sub.3).sub.2                                                        -3,5                          808 C(O) C(O) --C(CH.sub.3).sub.2 CN H --C.sub.6 H.sub.4 CH.sub.3 -4                                                           --C.sub.6 H.sub.4 F-4                                                           809 C(O) C(O) --C(CH.su                                                       b.3).sub.2 CN H                                                                --C.sub.6 H.sub.4                                                              CH.sub.3 -4 --C.sub.6                                                          H.sub.4 CH.sub.3 -4                                                             810 C(O) C(O) C(CH.sub.                                                       3)(CH.sub.2 CH.sub.3)CN                                                        H --C.sub.6 H.sub.5                                                            --C.sub.6 H.sub.5                                                               811 C(O) C(O) --C(CH.su                                                       b.3).sub.2 CN H                                                                2-thienyl --C.sub.6                                                            H.sub.4 CH.sub.3 -3                                                             812 C(O) C(O) --C(CH.su                                                       b.3).sub.2 CN H                                                                --C.sub.6 H.sub.4                                                              C.sub.2 H.sub.5 -4                                                             --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           813 C(O) C(O) --C(CH.su                                                       b.3).sub.2 CN H                                                                --C.sub.6 H.sub.4                                                              CH.sub.3 -2 --C.sub.6                                                          H.sub.3 (CH.sub.3).sub.2                                                        -3,5                          814 C(O) C(O) --C(CH.sub.3).sub.2 CN H --C.sub.6 H.sub.4 Cl-4 --C.sub.6                                                        h.sub.4 CH.sub.3 -3                                                             815 C(O) C(O) --C(CH.su                                                       b.3).sub.2 CN H                                                                --C.sub.6 H.sub.3                                                              F.sub.2 -2,6 --C.sub.6                                                         H.sub.4 Cl-4                   816 C(O) C(O) --C(CH.sub.3).sub.2 CN H --C.sub.6 H.sub.4 CH.sub.3 -2                                                           --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    817 C(O) C(O) --C(CH.sub.3).sub.2 CN H --C.sub.6 H.sub.4 NO.sub.2 -2                                                           --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    818 C(O) C(O) --C(CH.sub.3).sub.2 CN H --C.sub.6 H.sub.4 Cl-2 --C.sub.6                                                        H.sub.4 CH.sub.3 -3                                                             819 C(O) C(O) --C(CH.su                                                       b.3).sub.2 CO.sub.2                                                            CH.sub.3 H --C.sub.6                                                           H.sub.5 --C.sub.6                                                              H.sub.5                        820 C(O) C(O) C(CH.sub.3).sub.2 CH.sub.2 H --C.sub.6 H.sub.4 CH.sub.3                                                          -4 --C.sub.6 H.sub.4                                                           CH.sub.3 -4                       CH═CH.sub.2                                                             821 C(O) C(O) C(CH.sub.3).sub.2 CH.sub.2 H --C.sub.6 H.sub.4 CH.sub.3                                                          -3 --C.sub.6 H.sub.4                                                           CH.sub.3 -3                       CH═CH.sub.2                                                             822 C(O) C(O) C(CH.sub.3).sub.2 CH.sub.2 H --C.sub.6 H.sub.5 --C.sub.6                                                         H.sub.5                           CH═CH.sub.2                                                             823 C(O) C(O) --CH.sub.2 Si(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 C.sub.2                                                        H.sub.5 -4 --C.sub.6                                                           H.sub.3 NO.sub.2                                                               -2-CH.sub.3 -5                 824 C(O) C(O) --CH.sub.2 Si(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4                                                           --C.sub.6 H.sub.4 Cl-4                                                          825 C(O) C(O) --CH.sub.                                                       2 Si(CH.sub.3).sub.3 H                                                         --C.sub.6 H.sub.4                                                              CH.sub.3 -2 --C.sub.6                                                          H.sub.4 CH.sub.3 -2                                                             826 C(O) C(O) --CH.sub.                                                       2 Si(CH.sub.3).sub.3 H                                                         --C.sub.6 H.sub.4                                                              NO.sub.2 -2 --C.sub.6                                                          H.sub.4 NO.sub.2 -2                                                             827 C(O) C(O) --CH.sub.                                                       2 Si(CH.sub.3).sub.3 H                                                         --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.5                                                               828 C(O) C(O) --CH.sub.                                                       2 Si(CH.sub.3).sub.3 H                                                         --C.sub.6 H.sub.4                                                              C.sub.2 H.sub.5 -4                                                             --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           829 C(O) CH.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.5                                                               830 C(O) CH.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.4 Cl-4                                                          831 C(O) CH.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  832 C(O) CH.sub.2 --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                            H.sub.3 Cl.sub.2 -3,4                                                           833 C(O) CH.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.4                                                              CF.sub.3 -4                    834 C(O) CH.sub.2 --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                            H.sub.4 CO.sub.2                                                               CH.sub.3 -4                    835 C(O) CH.sub.2 --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                            H.sub.4 NO.sub.2 -2                                                             836 C(O) CH.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.4 F-4                                                           837 C(O) CH.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          2-furyl --C.sub.6                                                              H.sub.5                        838 C(O) CH.sub.2 --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                            H.sub.4 Br-2                   839 C(O) CH.sub.2 --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                            H.sub.4 CN-2                   840 C(O) CH.sub.2 --C(CH.sub.3).sub.3 H 2-thienyl --C.sub.6 H.sub.5                                                             841 C(O) CH.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.4                                                              CH.sub.3 -4 --C.sub.6                                                          H.sub.4 CN-4                   842 C(O) CH.sub.2 --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                          --C.sub.6 H.sub.5                                                               843 C(O) CH.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.4                                                              NO.sub.2 -3                    844 C(O) CH.sub.2 --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                            H.sub.4 OCH.sub.3 -4                                                            845 C(O) CH.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.4                                                              OCH.sub.3 -3                   846 C(O) CH.sub.2 --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                            H.sub.4 CH.sub.3 -3                                                             847 C(O) CH.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.4                                                              CH.sub.3 -4 --C.sub.6                                                          H.sub.4 CH.sub.3 -3                                                             848 C(O) CH.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.4                                                              CH.sub.3 -4                    849 C(O) CH.sub.2 --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                          --C.sub.6 H.sub.4                                                              CH.sub.3 -4                    850 C(O) CH.sub.2 --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 Cl.sub.2 -3,4                                                        --C.sub.6 H.sub.5                                                               851 C(O) CH.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.3                                                              Cl.sub.2 -3,4 --C.sub.6                                                        H.sub.4 CH.sub.3 -4                                                             852 C(O) CH.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          2-pyridyl --C.sub.6                                                            H.sub.5                        853 C(O) CH.sub.2 --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 2-pyridyl                                                             854 C(O) CH.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.4                                                              CH.sub.3 -2                    855 CH.sub.2 C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                            H.sub.5                        856 CH.sub.2 C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                            H.sub.4 F-4                    857 CH.sub.2 C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                            H.sub.4 Br-2                   858 CH.sub.2 C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                            H.sub.3 Cl.sub.2 -3,4                                                           859 CH.sub.2 C(O)                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.4                                                              CH.sub.3 -2                    860 CH.sub.2 C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -3                                                          --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,3                  861 CH.sub.2 C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -3                                                          --C.sub.6 H.sub.5                                                               862 CH.sub.2 C(O)                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.4                                                              CH.sub.3 -3 2-thienyl                                                           863 C(H) C(O) --C(CH.su                                                       b.3).sub.3 H 2-pyridyl                                                         --C.sub.6 H.sub.5                                                               864 C(H) C(O) --C(CH.su                                                       b.3).sub.3 -- --C.sub.6                                                        H.sub.5 --C.sub.6                                                              H.sub.5                        865 C(H) C(O) --C(CH.sub.3).sub.3 -- --C.sub.6 H.sub.5 --C.sub.6                                                               H.sub.4 F-4                    866 C(H) C(O) --C(CH.sub.3).sub.3 -- --C.sub.6 H.sub.5 --C.sub.6                                                               H.sub.3 Cl.sub.2 -3,4                                                           867 C(H) C(O) --C(CH.su                                                       b.3).sub.3 -- --C.sub.6                                                        H.sub.5 --C.sub.6                                                              H.sub.4 Br-2                   868 C(H) C(O) --C(CH.sub.3).sub.3 -- --C.sub.6 H.sub.4 CH.sub.3 -3                                                             --C.sub.6 H.sub.5                                                               869 C(H) C(O) --C(CH.su                                                       b.3).sub.3 -- --C.sub.6                                                        H.sub.5 2-thienyl                                                               870 C(O) CH.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --CH.sub.2 C.sub.6                                                             H.sub.5                        871 C(O) CH.sub.2 --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --CO.sub.2                                                           CH.sub.2 CH.sub.3                                                               872 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --N(H)C.sub                                                       .6 H.sub.5 CH.sub.3 -4                                                         --C.sub.6 H.sub.5                                                               873 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C(O)C.sub                                                       .6 H.sub.5 --C.sub.6                                                           H.sub.5                        874 C(O) C(O) --C(CH.sub.3).sub.3 H --C(O)C.sub.6 H.sub.5 --C.sub.6                                                            H.sub.4 CH.sub.3 -3                                                             875 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 --C(O)C.sub.6                                                            H.sub.5                        876 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -4                                                              --C(O)C.sub.6 H.sub.5                                                           877 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 C.sub.2 H.sub.5                                                        -4 --C(O)C.sub.6                                                               H.sub.5                        878 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C(O)C.sub.6                                                            H.sub.5                        879 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 (CH.sub.3).sub.2                                                         -2,3 2-methyl-1-phenyl-              1-propyl                                                                 880 C(O) C(O) --C(CH.sub.3).sub.3 H 2-(1,2,3,4-tetrahydro0 --C.sub.6                                                           H.sub.4 CH.sub.3 -3                                                                  naphthyl                 881 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 --CH.sub.2                                                          C.sub.6 H.sub.5                                                                 882 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --CHClC.sub.6                                                          H.sub.5                        883 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --CH.sub.2                                                               C.sub.6 H.sub.5                                                                 884 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 Cl-4 --CHClC.sub                                                       .6 H.sub.5                     885 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.13 (CH.sub.3).sub.2                                                        -2,3 --CH.sub.2 C.sub.6                                                        H.sub.5                        886 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 C.sub.2 H.sub.5                                                          -4 --CH.sub.2 C.sub.6                                                          H.sub.5                        887 C(OC(O)CH.sub.3) C(O) --C(CH.sub.3).sub.3 -- --C.sub.6 H.sub.5                                                             --C.sub.6 H.sub.5                                                               888 C(OCO.sub.2                                                               CH.sub.3) C(O) --C(CH.su                                                       b.3).sub.3 -- --C.sub.6                                                        H.sub.5 --C.sub.6                                                              H.sub.5                        889 C(OC(O)CH.sub.2 OCH.sub.3) C(O) --C(CH.sub.3).sub.3 -- --C.sub.6                                                           H.sub.5 --C.sub.6                                                              H.sub.5                        890 C(OCO.sub.2 CH═CH.sub.2) C(O) --C(CH.sub.3).sub.3 -- --C.sub.6                                                         H.sub.5 --C{hd 6 H5                                                             891 C(OC(O)CH═CHCH.                                                       sub.3) C(O) --C(CH.sub.3                                                       ).sub.3 -- --C.sub.6                                                           H.sub.5 --C.sub.6 H5                                                            892 C(OC(O)CH═C(CH.                                                       sub.3).sub.2) C(O)                                                             --C(CH.sub.3).sub.3 --                                                         --C.sub.6 H.sub.5                                                              --C.sub.6 H5                   893 C(OC(O)-2-furyl C(O) --C(CH.sub.3).sub.3 -- --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.5                                                               894 C(OC(O)CH(CH.sub.3)                                                       ═CH.sub.2) C(O)                                                            --C(CH.sub.3).sub.3 --                                                         --Chd 6 H.sub.4 C.sub.2                                                        H.sub.5 -4 --C.sub.6                                                           H.sub.3 (CH.sub.3).sub.2                                                        -3,5                          895 C(OC(O)CH.sub.3) C(O) --C(CH.sub.3).sub.3 -- --C.sub.6 H.sub.4                                                             C.sub.2 H.sub.5 -4                                                             --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           896 C(OCO.sub.2                                                               CH.sub.3) C(O) --C(CH.su                                                       b.3).sub.3 -- --C.sub.6                                                        H.sub.4 C.sub.2 H.sub.5                                                        -4 --C.sub.6 H.sub.3                                                           (CH.sub.3).sub.2 -3,5                                                           897 C(OC(O)CH.sub.2                                                           OCH.sub.3) C(O)                                                                --C(CH.sub.3).sub.3 --                                                         --C.sub.6 H.sub.4                                                              C.sub.2 H.sub.5 -4                                                             --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           898 C(OCO.sub.2                                                               CH═CH.sub.2) C(O)                                                          --C(CH.sub.3).sub.3 --                                                         --C.sub.6 H.sub.4                                                              C.sub.2 H.sub.5 -4                                                             --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           899 C(OC(O)-2-furyl                                                           C(O) --C(CH.sub.3).sub.3                                                        -- --C.sub.6 H.sub.4                                                          C.sub.2 H.sub.5 -4                                                             --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           900 C(OC(O)CH.sub.2                                                           CH.sub.3) C(O) --C(CH.su                                                       b.3).sub.3 -- --C.sub.6                                                        H.sub.4 C.sub.2 H.sub.5                                                        -4 --C.sub.6 H.sub.3                                                           (CH.sub.3).sub.2 -3,5                                                           901 C(OC(O)CH.sub.3)                                                          C(O) --C(CH.sub.3).sub.3                                                        -- --C.sub.6 H.sub.3                                                          (CH.sub.3).sub.2 -2,3                                                          --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    902 C(OCO.sub.2 CH.sub.3) C(O) --C(CH.sub.3).sub.3 -- --C.sub.6 H.sub.3                                                        (CH.sub.3).sub.2 -2,3                                                          --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    903 C(OC(O)-2-furyl C(O) --C(CH.sub.3).sub.3 -- --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -2,3                                                          --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    904 C(OC.sub.2 H.sub.5) C(O) --C(CH.sub.3).sub.3--  --C.sub.6 H.sub.3                                                          (CH.sub.3).sub.2 -2,3                                                          --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  905 C(OCH.sub.3) C(O) --C(CH.sub.3).sub.3 -- --C.sub.6 H.sub.3 (CH.sub.3                                                       ).sub.2 -2,3 --C.sub.6                                                         H.sub.3 Cl.sub.2 -2,4                                                           906 C(OCH.sub.3) C(O)                                                         --C(CH.sub.3).sub.3 --                                                         --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.5                                                               907 C(OC(O)CH═CH.su                                                       b.2) C(O) --C(CH.sub.3).                                                       sub.3 -- --C.sub.6                                                             H.sub.5 -4 --C.sub.6                                                           H.sub.3 (CH.sub.3).sub.2                                                        -2,3                          908 C(OC(O)CH═CH.sub.2) C(O) --C(CH.sub.3).sub.3 -- --C.sub.6                                                              H.sub.5 --C.sub.6                                                              H.sub.5                        909 C(OC(O)C.sub.6 H.sub.4 C.sub.2 H.sub.5 -4) C(O) --C(CH.sub.3).sub.3                                                        -- --C.sub.6 H.sub.5                                                           --C.sub.6 H.sub.5                                                               910 C(OC(O)CH.sub.2                                                           CH═CH.sub.2) C(O)                                                          --C(CH.sub.3).sub.3 --                                                         --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.5                                                               911 C(OC(O)CH═C(CH.                                                       sub.3).sub.2)  C(O)                                                            --C(CH.sub.3).sub.3 --                                                         --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.5                                                               912 C(OC(O)CH.sub.3)                                                          C(O) --C(CH.sub.3).sub.3                                                        -- --C.sub.6 H.sub.5                                                          --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  913 C(OC(O)CCH.sub.3 ═CH.sub.2) C(O) --C(CH.sub.3).sub.3 --                                                                --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.3                                                              Cl.sub.2 -2,4                  914 SO.sub.2 C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6                                                            H.sub.5                        915 SO.sub.2 C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 CH.sub.3 -4                                                          --C.sub.6 H.sub.5                                                               916 SO.sub.2 C(O)                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.4 F-4                                                          --C.sub.6 H.sub.5                                                               917 C(O) SO.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.4 F-4                                                           918 C(O) SO.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.5                                                               919 C(O) SO.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              --C.sub.6 H.sub.4                                                              CH.sub.3 -4                    920 C(O) SO.sub.2 --C(CH.sub.3).sub.3 H 2-pyridyl --C.sub.6 H.sub.5                                                             921 C(O) SO.sub.2                                                             --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5                                                              2-thienyl                      922 C(O) P(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --NHC.sub.6                                                              H.sub.4 Cl-2                     CH.sub.3                                                                     923 P(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.5         CH.sub.3                                                                      924 C(O) C(O) --CH.sub.3 H --C.sub.6 H.sub.4 Cl-4 --C.sub.6 H.sub.4                                                            Cl-4                           925 C(O) C(O) --CH.sub.3 H --C.sub.6 H.sub.2 Cl.sub.2 -3,5 --C.sub.6                                                           H.sub.2 Cl.sub.2 -3,5                                                           926 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --CH.sub.2                                                        CH.sub.2 CH.sub.2                                                              CH.sub.3 --CH.sub.2                                                            CH.sub.2 CH.sub.2                                                              CH.sub.3                       927 C(O) C(O) --C(CH.sub.3).sub.3 H heptyl heptyl                              928 C(O) C(O) --C(CH.sub.3).sub.3 H --CH.sub.2 Cl --CH.sub.2 Cl                                                                 929 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --CH.sub.2                                                        CH.sub.2 CH.sub.2                                                              CH.sub.3 2-furyl                                                                930 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --OCH.sub.2                                                        CH.sub.3 --CH.sub.2                                                           CH.sub.2 CH.sub.2                                                              CH.sub.3                       931 C(O) C(O) --C(CH.sub.3).sub.3 H --OCH.sub.2 CH.sub.3 --C.sub.6                                                             H.sub.4 Cl-4                   932 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --OCH.sub.2                                                              CH.sub.3                       933 C(O) C(O) --C(CH.sub.3).sub.3 H CH(C.sub.6 H.sub.5)CH(CH.sub.3)                                                            --C.sub.6 H.sub.4                                                              CH.sub.3 -3                         CH.sub.2 CH.sub.3                                                         934 C(O) C(O) --C(CH.sub.3).sub.3 H --OC.sub.6 H.sub.5 --C.sub.6                                                               H.sub.5                        935 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --OC.sub.6                                                               H.sub.5                        936 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --OC.sub.6                                                               H.sub.4 NO.sub.2 -4                                                             937 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --CH═C(                                                       CH.sub.3).sub.2                                                                --CH═C(CH.sub.3).sub                                                       .2                             938 C(O) C(O) --C(CH.sub.3).sub.3 H --CCl═CCl.sub.2  --CCl═CCl.s                                                       ub.2                           939 C(O) C(O) --C(CH.sub.3).sub.3 H --CH═CHC.sub.6 H.sub.5 --CH═                                                       CHC.sub.6 H.sub.5                                                               940 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.4 CH.sub.3 -4                                                            --C═CC.sub.6                                                               H.sub.5                        941 C(O) C(O) --C(CH.sub.3).sub.3 H --C═CC.sub.6 H.sub.5 --C.sub.6                                                         H.sub.4 CH.sub.3 -5                                                             942 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -2,3 --C═CC.sub.6                                                         H.sub.5                        943 C(O) C(O) --C(CH.sub.3).sub.3 H cyclohexyl cyclohexyl                      944 C(O) C(O) --C(CH.sub.3).sub.3 H 3,4-epoxy --C.sub.6 H.sub.4                                                                CH.sub.3 -3                         cyclohexyl                                                                945 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl --C.sub.6                                                             H.sub.4 C.sub.6 H.sub.5                                                        -4                             946 C(O) C(O) --C(CH.sub.3).sub.3 H --H.sub.6 H.sub.5 1,2,3,4-tetrahydro                                                       -                              947 C(O) C(O) --C(CH.sub.3).sub.3 H 2-azolidinyl --C.sub.6 H.sub.4                                                             CH.sub.3 -3                    948 C(O) C(O) --C(CH.sub.3).sub.3 H 2,2-dimethyl-4- --CH.sub.4 CH.sub.3                                                        -3                                  keto-2,3-dihydro-                                                              pyranyl                                                                   949 C(O) C(O) --C(CH.sub.3).sub.3 H 2-furyl 2-furyl                            950 C(O) C(O) --C(CH.sub.3).sub.3 H 2-thienyl 2-thienyl                        951 C(O) C(O) --C(CH.sub.3).sub.3 H azolidinyl azolidinyl                      952 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --N(CH.sub.2                                                             CH.sub.3).sub.2                                                                 953 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 --NHC.sub.6                                                            H.sub.4 Cl-4                   954 C(O) C(O) --C(CH.sub.3).sub.3 H --N(CH.sub.2 CH.sub.3).sub.2                                                               --N(CH.sub.2 CH.sub.3).s                                                       ub.2                           955 C(O) C(O) 1,2-diphenyl- H --C.sub.6 H.sub.5 --C.sub.6 H.sub.5                                                                  ethyl                      956 C(O) C(O) cyclopentyl H --C.sub.6 H.sub.5 --C.sub.6 H.sub.5                                                                 957 C(O) C(O) cyclohexy                                                       l H --C.sub.6 H.sub.5                                                          --C.sub.6 H.sub.5                                                               958 C(O) C(O) 2-methyl                                                        H --C.sub.6 H.sub.5                                                            --C.sub.6 H.sub.5                                                                  cyclohexyl                 959 C(O) C(O) 2-methylphenyl H --C.sub.6 H.sub.5 --C.sub.6 H.sub.5                                                              960 C(O) C(O) cyclopeny                                                       l- H --C.sub.6 H.sub.5                                                         --C.sub.6 H.sub.5                                                                  phenylmethyl                                                                961 C(O) C(O) --C.sub.6                                                        H.sub.5 H --C.sub.6                                                           H.sub.5 --C.sub.6                                                              H.sub.5                        962 C(O) C(O) --C.sub.6 H.sub.5 H --C.sub.6 H.sub.3 Cl.sub.2 -3,5                                                              --C.sub.6 H.sub.3                                                              Cl.sub.2 3,5                   963 C(O) C(O) --C.sub.6 G.sub.4 Cl H --C.sub.6 H.sub.5 --C.sub.6                                                               H.sub.5                        964 C(O) C(O) --C.sub.6 H.sub.4 Cl-4 H --C.sub.6 H.sub.5 --C.sub.6                                                             H.sub.5                        965 C(O) C(O) --CH.sub.2 C.sub.6 H.sub.5 H --C.sub.6 H.sub.5 --C.sub.6                                                         H.sub.5                        966 C(O) C(O) --CH.sub.2 C.sub.6 H.sub.5 H --C.sub.6 H.sub.3 Cl.sub.2                                                          -3,5 --CH.sub.2 Cl                                                              967 C(O) C(O) --CH.sub.                                                       2 C.sub.6 H.sub.5 H                                                            --C.sub.6 H.sub.3                                                              Cl.sub.2 03,5 --C.sub.6                                                        H.sub.3 Cl.sub.2 -3,5                                                           968 C(O) C(O) 6-Cl-3-py                                                       ridizinyl H --C.sub.6                                                          H.sub.5 --H.sub.6                                                              H.sub.5                        969 C(O) C(O) --CH.sub.2 C(CH.sub.3)═CH.sub.2 H --C.sub.6 H.sub.4                                                          CH.sub.3 -4 --C.sub.6                                                          H.sub.5                        970 C(O) C(O) --CH.sub.2 C(CH.sub.3)═CH.sub.2 H --C.sub.6 H.sub.4                                                          CH.sub.3 -4 --C.sub.6                                                          H.sub.4 CH.sub.3 -3                                                             971 C(O) C(O) C(CH.sub.                                                       3)═CHCH.sub.2                                                              CH.sub.2 CH H --C.sub.6                                                        H.sub.5 --C.sub.6                                                              H.sub.4 Br-2                      (CH.sub.3)CH.sub.2 CH.sub.3                                                 972 C(O) C(O) C(CH.sub.3)═CHCH.sub.2 CH.sub.2 CH H --C.sub.6                                                               H.sub.5 --C.sub.6                                                              H.sub.4 NO.sub.2 -2                                                                (CH.sub.3)CH.sub.2                                                         CH.sub.3                       973 C(O) C(O) --CH.sub.2 C(CH.sub.3).sub.2 Br H --C.sub.6 H.sub.4                                                              CH.sub.3 -4 --C.sub.6                                                          H.sub.4 CH.sub.3 -3                                                             974 C(O) C(O) --CH(CH.s                                                       ub.3)CO.sub.2 CH.sub.2                                                         CH.sub.3 H --C.sub.6                                                           H.sub.4 CH.sub.3 -4                                                            --C.sub.6 H.sub.5                                                               975 C(O) C(O) --CH(CH.s                                                       ub.3)CO.sub.2 CH.sub.2                                                         CH.sub.3 H --C.sub.6                                                           H.sub.4 CH.sub.3 -4                                                            --C.sub.6 H.sub.4                                                              NO.sub.2 -2                    976 C(O) C(O) --CH(CH.sub.3)CH.sub.2 N(CH.sub.3).sub.2 H --C.sub.6                                                             H.sub.4 CH.sub.3 -4                                                            --C.sub.6 H.sub.3                                                              (CH.sub.3).sub.2 -3,5                                                           977 C(O) C(O) --CH(CH.s                                                       ub.3)C(CH.sub.3).sub.2                                                         OH H --C.sub.6 H.sub.4                                                         CH.sub.3 -4  --C.sub.6                                                         H.sub.5                        978 C(O) C(O) --CH(CH.sub.3)C(CH.sub.3).sub.2 OH H --C.sub.6 H.sub.4                                                           CH.sub.3 -4  --C.sub.6                                                         H.sub.3 (CH.sub.3).sub.2                                                        -3,5                          979 C(S) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.5        980 C(S) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                        Br-2                           981 C(S) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        Cl.sub.2 -2,4                  982 C(S) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        Cl.sub.2 -3,4                  983 C(S) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        F.sub.2 -2,6                   984 C(S) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --C.sub.6 H.sub.3                                                        CH.sub.3 -4                    987 C(S) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --NHCH.sub.2                                                             CH.sub.3                       988 C(S) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --NHCH.sub.2                                                             CH.sub.2 CH.sub.3                                                               989 C(S) C(O) --C(CH.su                                                       b.3).sub.3 H --C.sub.6                                                         H.sub.5 NHCH.sub.2                                                             CH.sub.2 CH.sub.2                                                              CH.sub.3                       990 C(O) C(O) --C(CH.sub.3).sub.3 H --CH.sub.2 CH.sub.2 CH.sub.3                                                               CH.sub.2 CH.sub.2                                                              CH.sub.3                       991 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --CH.sub.2 Cl                                                             992 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --C(CH.sub.                                                       3).sub.2 Br --C.sub.6                                                          H.sub.5                        993 C(O) C(O) --C(CH.sub.3).sub.3 H --CH.sub.2 CH.sub.2 CH.sub.2                                                               CH.sub.3 --OC.sub.2                                                            H.sub.5                        994 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 Cl-4 --OC.sub.2                                                          H.sub.5                        995 C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.3 F.sub.2 -2,6                                                             --OC.sub.2 H.sub.5                                                              996 C(O) C(O) --C(CH.su                                                       b.2).sub.2 C.sub.6                                                             H.sub.5 H --C.sub.6                                                            H.sub.5 --C.sub.6                                                              H.sub.5                        997 C(O) C(O) --C(CH.sub.2).sub.2 C.sub.6 H.sub.5 H --C.sub.6 H.sub.5                                                          --C.sub.6 H.sub.4 Cl-4                                                          998 C(O) C(O) --C(CH.su                                                       b.2).sub.2 C.sub.6                                                             H.sub.5 H --C.sub.6                                                            H.sub.5 --C.sub.6                                                              H.sub.3 Cl.sub.2 -3,4                                                           999 C(O) C(O) --C(CH.su                                                       b.3).sub.3 H --NH.sub.2                                                        --C.sub.6 H.sub.4 Cl-4                                                          1000  C(O) C(O)                                                               --C(CH.sub.3).sub.3 H                                                          --NHSO.sub.2 C.sub.6                                                           H.sub.5 --C.sub.6                                                              H.sub.4 CH.sub.3 -3                                                             1001  C(O) C(O)                                                               --C(CH.sub.3).sub.3 H                                                          --NHSO.sub.2 C.sub.6                                                           H.sub.4 Cl-2 --C.sub.6                                                         H.sub.4 CH.sub.3 -3                                                             1002  C(O) C(O)                                                               --C(CH.sub.3).sub.3 H                                                          --NHSO.sub.2 C.sub.6                                                           H.sub.4 Cl-4 --C.sub.6                                                         H.sub.4 CH.sub.3 -3                                                             1003  C(O) C(O)                                                               --C(CH.sub.3).sub.3 H                                                          NHSO.sub.2 C.sub.6                                                             H.sub.4 CH.sub.3 -4                                                            --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    1004  C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.5 --NHCH.sub.2                                                           CH.sub.2 CH.sub.3                                                               1005  C(O) C(O)                                                               --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.5 Cl-3                                                         --NHCH.sub.2 CH.sub.2                                                          CH.sub.3                       1006  C(O) C(O) --C(CH.sub.3).sub.3 H --C.sub.6 H.sub.4 CH.sub.3 -3                                                            --NHC.sub.6 H.sub.5                                                             1007  C(O) C(O)                                                               --C(CH.sub.3).sub.3 H                                                          --C.sub.6 H.sub.4                                                              CH.sub.3 -3 --NHCH.sub.2                                                        CH.sub.2 CH.sub.3                                                              1008  C(O) C(O)                                                               C(CH.sub.3).sub.2                                                              C(O)NH.sub.2 H --NHC(O)C                                                       .sub.6 H.sub.4 Cl-4                                                            --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    1009  C(O) C(O) C(CH.sub.3).sub.2 C(O)NH.sub.2 H  NHC(O)C.sub.6 H.sub.4                                                        CH.sub.3 -2 --C.sub.6                                                          H.sub.4 CH.sub.3 -3                                                             1010  C(O) C(O)                                                               C(CH.sub.3).sub.2                                                              C(O)NH.sub.2 H --C.sub.6                                                        H.sub.4 NO.sub.2 -2                                                           --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    1011  C(O) C(O) C(CH.sub.3).sub.2 C(O)NH.sub.2 H --C.sub.6 H.sub.4 Cl-2                                                        --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    1012  C(H) C(O) --C(CH.sub.3).sub.3 -- --C.sub.6 H.sub.5 CH.sub.3 -2                                                           --NHCH.sub.2 CH.sub.2                                                          CH.sub.3                       1013  C(H) C(O) --C(CH.sub.3).sub.3 -- --C(Cl)═C(Cl)CO.sub.2 H                                                             --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    1014  C(H) C(O) --C(CH.sub.3).sub.3 -- --C(Br)═C(Br)CO.sub.2 H                                                             --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    1015  C(CH.sub.3).sub.3 C(O) --C(CH.sub.3).sub.3 -- --C(O)C.sub.2                                                              H.sub.5 --C.sub.6                                                              H.sub.4 CH.sub.3 -3                                                             1016  C(CH.sub.3).sub.3                                                        C(O) --C(CH.sub.3).sub.                                                       3 -- --CH.sub.3                                                                --C.sub.6 H.sub.4                                                              CH.sub.3 -3                    1017  CH(CH.sub.3).sub.2 C(O) --C(CH.sub.3).sub.3 H --CH.sub.3 --C.sub.6                                                        H.sub.4 CH.sub.3 -3                                                            1018  CH(CH.sub.3).sub.                                                       2 C(O) --C(CH.sub.3).sub                                                       .3 H --CN --C.sub.6                                                            H.sub.5                      __________________________________________________________________________

EXAMPLE NO. 1 Preparation of N'-t-butyl-N,N'-(4-chlorobenzoyl)hydrazine

A suspension of t-butylhydrazine hydrochloride (12.5 g, 0.1 mole) in toluene (100 ml) at 0-5° C. was treated slowly with 1 equivalent of NaOH solution, prepared from diluting 8 g of 50% NaOH commercially available solution to 20 ml of the volume with H₂ O. At 0 to 5° C. with mechanical stirring, 2 equivalents of 4-chlorobenzoyl chloride (35.9 g, 0.2 mole) and 2 equivalents of NaOH (16 g of 50% NaOH diluted with H₂ O to 40 ml) were added dropwise separately and simultaneously from dropping funnels. The exothermic reaction was cooled down by an ice-water bath through the entire addition. After the addition was completed, the resulting suspension was stirred at room temperature (RT) for one hour. The white precipitate (p.p.t.) was collected by suction-filtration and washed with a small amount of toluene and 100 ml of H₂ O. The material was then air-dried, then crystallized from 95% aqueous CH₃ OH to afford 24.65 g of N'-t-butyl-N,N'-(4-chlorobenzoyl)hydrazine as needles: m.p. 246-248° C.

Additional product can be obtained by concentrating the mother liquor of crystallization.

EXAMPLE NO. 3 Preparation of N'-t-butyl-N,N'-dibenzoyl-hydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (1.24 g, 10 mmoles) in toluene (50 ml) at room temperature, was added dropwise a solution of 50% aqueous sodium hydroxide (0.8 g, 10 ml). After 15 minutes, the reaction mixture was cooled to 5° C. and solutions of benzoyl chloride (2.82 gm, 20 ml) in toluene (7 ml) and 50% aqueous sodium hydroxide (1.6 g) were added dropwise and simultaneously from separate addition funnels while maintaining the temperature below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction mixture was diluted with ether and the product isolated by filtration. The product was washed with water and ether and dried. The product was recrystallized from ethermethanol to afford N'-t-butyl-N,N'-dibenzoylhydrazine as a white powder: m.p. 174-176° C.

EXAMPLE NO. 16 Preparation of N'-t-butyl-N'-(4-chlorobenzoyl)-N-benzoylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (1.24 g, 10 mmoles) in toluene (30 ml) at room temperature was added dropwise a 50% aqueous solution of sodium hydroxide (0.8 g, 10 mmole). After 15 min., the reaction mixture was cooled to 5° C. and a solution of benzoyl chloride (1.42 g, 10 mmoles) in toluene (5 ml) and a solution of aqueous 50% sodium hydroxide (0.8 g, 10 mmole) were added dropwise simultaneously from separate addition funnels while maintaining the temperature at or below 10°. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction mixture was diluted with toluene washed with water. The organic layer was separated, dried over anhydrous magnesium sulfate, and the solvent removed under vacuum to afford a yellow oil which slowly solidifies on standing. The product was recrystallized from ether-hexane to afford white crystals.

To a stirred solution of the monobenzoylated compound (1.92 g, 10 mmoles) in toluene (30 ml) at 5° C., were added dropwise simultaneously from separate addition funnels, solutions of p-chlorobenzoyl chloride (1.75 g, 10 mmoles) in toluene (5 ml) and aqueous 50% sodium hydroxide solution (0.8 g) while maintaining the temperature below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The mixture was then diluted with hexane and the precipitated product isolated by filtration. The product was washed with water and hexane and dried. The crude product was recrystallized from ether-methanol to afford N'-t-butyl-N'-(4-chlorobenzoyl)-N-benzoylhydrazine as a white powder: m.p. 201-204° C.

EXAMPLE NO. 44 Preparation of N'-neopentyl-N,N'-dibenzoylhydrazine

A solution of benzoylhydrazine (1.36 g, 10 mmoles), 1,1,1-trimethylacetaldehyde (0.86 g, 10 mmoles), and acetic acid (catalytic amount) in methanol are stirred at room temperature until hydrazone formation is complete. The reaction mixture is brought to a pH of 4 and sodium cyanoborohydride (0.75 g, 12.5 mmoles) is added slowly portionwise (the reaction is connected to an aqueous sodium hydroxide trap). Upon completion, the reaction is diluted with excess aqueous sodium hydroxide and the methanol is removed under vacuum. The product is partitioned into methylene chloride and washed with aqueous base and water. The organic layer is separated and dried over anhydrous magnesium sulfate. The magnesium sulfate is filtered, and the methylene chloride removed under vacuum to afford the product as a yellow oil which solidifies on standing. The crude 2-neopentyl-1-benzoylhydrazine is benzoylated directly.

To a stirred solution of the 2-neopentyl-1-benzoylhydrazine in toluene (40 ml) at 5° C., were added dropwise and simultaneously solutions of benzoyl chloride (1.4 g, 10 mmoles) in toluene (5 ml) and aqueous 50% sodium hydroxide solution (0.8 g) while maintaining the temperature below 10° C. After the addition, the reaction mixture was warmed to room temperature and stirred for 1 hour. The reaction mixture was diluted with hexane and the precipitated product isolated by filtration. The product was washed with water and hexane and dried. The crude product was recrystallized from methanol to afford N'-neopentyl-N,N'-dibenzoylhydrazine as a white powder: m.p. 237-239° C.

EXAMPLE NO. 102 Preparation of N'-t-butyl-N'-benzoyl-N-4-chlorothiobenzolyhydrazine

A mixture of 4-chloro-methylthio-thiobenzoate (3.0 g, 0.015 mol) and t-butyl hydrazine hydrochloride (2.0 g, 0.016 mol) in 5 ml of pyridine was heated at 90° C. for 18 hours. The mixture was poured into 0.1 N HCl/ether. The layers were separated and the organic extracts were washed with 3 portions of 0.1N HCl followed by saturated aqueous NaHCO. After the extracts were dried over anhydrous magnesium sulfate, the solvents were removed under vacuum to afford 1.9 g of a brown solid. Chromatography on silica gel using ether (25%)-methylene chloride (25%)-hexane as eluant afforded 0.8 g of a golden yellow solid. The solid was dissolved in 3 ml of methylene chloride and treated with pyridine (1 ml) and benzoyl chloride (0.6 ml). After 24 hours at 23° C., the reaction mixture was poured onto 0.1N HCl/ether. The organic layer was washed with saturated aqueous sodium bicarbonate and was dried over anhydrous magnesium sulfate. Evaporation of solvents gave a yellow oil which was chromatographed on silica gel using ether (25%)-methylene chloride (25%)-hexane as eluant to give 0.15 g of N'-t-butyl-N'-benzoyl-N-4-chlorothiobenzoylhydrazine as a yellow solid: m.p. 160-162° C.

EXAMPLE NO. 103 Preparation of N'-t-butyl-N'-thiobenzoyl-N-benzoylhydrazine

A mixture of N'-t-butyl-N-benzoyl hydrazine (60% purity, 1.0 g, 0.0031 mol) and S-(thiobenzoyl)-thioglycolic acid (1.0 g, 0.0047 mol) in 3 ml of pyridine was heated at about 90° C. for 24 hours. The dark colored mixture was cooled and poured into 0.1 N HCl/ether. The organic layer was washed with three 15 ml portions of 0.1 N HCl followed by saturated aqueous sodium bicarbonate. The organic extracts were dried over anhydrous magnesium sulfate. Evaporation of the solvents afforded 0.5 g of a brown oil which was recrystallized from ether-hexane to yield 0.2 g of N'-t-butyl-N'-thiobenzoyl-N-benzoylhydrazine as a tan solid m.p. 169-171° C.

EXAMPLE NO. 148 Preparation of N'-t-butyl-N-(2-hydroxy-methylbenzoyl)-N'-benzoylhydrazine

t-Butylhydrazine (0.1 mol) in 75 ml ethanol was treated with 50% aqueous sodium hydroxide (0.11 mol). Phthalide (0.1 mol) was added and the mixture was refluxed for 5 days. After cooling, water was added and the crude product was isolated by filtration. Filtration through silica gel afforded N'-t-butyl-N-(2-hydroxymethylbenzoyl)hydrazine (3.0 g). m.p. 116-118° C.

0.7 g of N'-t-butyl-N-(2-hydroxymethylbenzoyl)hydrazine and 1.1 g benzoyl chloride are combined in 10 ml of 5% NaOH and stirred at room temperature for 1.5 hours. The solids are filtered off, washed with water, then ether, to afford 0.6 g of white solid N'-t-butyl-N-(2-(benzoyloxymethyl)benzoyl)-N'-benzoylhydrazine. m.p. 190-191° C.

EXAMPLE NO. 220 Preparation of N-(3-toluoyl)-N'-t-butyl-N'-benzoylhydrazine

Step 1

To a stirred suspension of t-butylhydrazine (51 g) in a mixture of dioxane and water (2:1) (150 ml) was added sodium hydroxide (32 g of a 50% aqueous solution). After 10 min., the solution was cooled to 5° C. and di-t-butyldicarbonate (42 g) was added dropwise so as to maintain the reaction temperature below 10° C. The reaction mixture was warmed and stirred 2 hours at room temperature. The reaction mixture was filtered, washed with water and dried to afford N-t-butyloxycarbonyl-N'-t-butylhydrazine (74 g) as a white crystalline solid. m.p. 69-71° C.

Step 2

To a stirred solution of N-t-butyloxycarbonyl-N'-t-butylhydrazine (61 g) in toluene (120 ml) was added benzoyl chloride (45 g) and sodium hydroxide (31 g of a 50% aqueous sodium hydroxide solution) dropwise and simultaneously. After stirring for 1 hour at room temperature, the solid N-t-butyloxycarbonyl-N'-t-butyl-N'-benzoylhydrazine was filtered, washed with water, hexane and dried to afford 52 g of product. m.p. 167-170° C.

Step 3

The N-t-butoxycarbonyl-N'-t-butyl-N'-benzoylhydrazine (52 g, 0.18 mol) was stirred at room temperature in a methanolic hydrochloric acid solution for 4 days. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate. The white precipitate was filtered, washed with water and dried in vacuo to give 30 g of N'-t-butyl-N'-benzoylhydrazine. m.p. 124-125° C.

Step 4

To a stirred mixture of N'-t-butyl-N'-benzoylhydrazine (1.0 g) in 15 ml toluene and aqueous sodium hydroxide (0.5 g of 50% NaOH) was added 3-toluoylchloride (0.9 g). After stirring for 2 hours, the product was isolated by filtration to give N'-t-butyl-N-(3-toluoyl)-N'-benzoylhydrazine in good yield. m.p. 111-114° C.

EXAMPLE NO. 295 Preparation of N'-(1,1-dimethylethyl)-N,N'-dibenzoylhydrazine

To a gentle refluxing solution of ethyl magnesium bromide (150 ml of 1M solution) was added acetone azine (20 g) dissolved in diethyl ether (80 ml). The solution was refluxed for three days. Upon cooling, a saturated solution of ammonium chloride (75 ml) was added. The aqueous layer was separated and washed twice with diethyl ether (150 ml). The combined ether extracts were dried over anhydrous magnesium sulfate, filtered and the ether removed at reduced pressure. The product was distilled through a vigreux column at 3 torr and collected in a dry ice/acetone cooled receiving flask. The boiling point was 40-50°. 15 g of product was collected.

Oxalic acid (17 g) was dissolved in a solution of ethanol:diethyl ether (1:1) (150 ml) and water (3.3 g) was added. To this acid solution was added the hydrazone (13 g) dissolved in diethyl ether (30 ml). The solution was stirred for 24 hours then filtered. The solid is washed once with diethyl ether. The filtrate was concentrated and combined with the solid to afford a 77% yield (16.3 g) of the hydrazine oxalate.

The 1,1-dimethylethylhydrazine oxalate (2 g) was dissolved in toluene and neutralized with 50% aqueous sodium hydroxide. To this solution was added benzoyl chloride (4.02 g) and sodium hydroxide (50% Aq. solution) (2.45 g) at 25° C. The reaction mixture was warmed to room temperature and stirred 3 hours. The mixture was diluted with hexane and filtered to afford the product as a white solid (0.5 g).

EXAMPLE NO. 324 Preparation of N'-t-butyl-N-(thio-benzoyl)-N'-(3-toluoyl)hydrazine

S-(thiobenzoyl)thioglycolic acid (3.0 g) was dissolved in 20 ml pyridine, treated with t-butyl hydrazine hydrochloride (excess, ca. 4 g) and then was heated at ca. 120° C. for 14 hours. Water (120 ml) was added and the mixture was extracted with ether. The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated to give crude N'-t-butyl-N-(thiobenzoyl)hydrazine as a viscous yellow oil.

N't-butyl-N-(thiobenzoyl)hydrazine (ca. 1 g), m-toluoyl chloride (approx. 0.7 g) and 50% aqueous sodium hydroxide (6 drops) were mixed in 1 ml water and 10 ml toluene at 23° C. After stirring for 3 hours, ether-hexane was added and the product was isolated by filtration (0.25 g). m.p. 165-168° C.

EXAMPLE NO. 344 Preparation of N'-t-butyl-N-[3-(N,N-dimethylcarbamoyl)benzoyl])-N'-benzoylhydrazine

N-(3-hydroxybenzoyl)-N'-t-butyl-N'-benzoylhydrazine (0.2 g) was stirred in tetrahydrofuran (15 ml) at 23° C. Solid potassium t-butoxide (0.1 g) was added and the solution went from clear colorless to cloudy yellow. After stirring 10 minutes at room temperature, N,N-dimethylcarbamoyl chloride was added dropwise (0.1 g). With the addition the solution turned colorless and a precipitate appeared. Saturated aqueous NaHCO3 and ether were added, the layers separated and the organic dried over magnesium sulfate, filtered and rotavapped to afford an oily solid.

EXAMPLE NO. 625 Preparation of N'-t-butyl-N-(4-(4,4-dimethyloxazol-2-yl)benzoyl)-N'-(3-toluoyl)hydrazine

1.2 g of N'-t-butyl-N-(4-carbomethoxybenzoyl)-N'-(3-toluoyl)hydrazine was heated in 2 ml of 2-amino-2-methyl-1-propanol at 90-100° C. for 5 hours. After cooling, the mixture was diluted with ether/methylene chloride and washed with 0.1 N HCl. The organic layer was evaporated to afford 1.0 g of the corresponding amide.

The amide in 10 ml of chloroform was treated with 0.25 g of thionyl chloride and stirred at 23° C. for 1.5 hours. Saturated aqueous sodium bicarbonate was added and the layers separated. Evaporation of the organic layer afforded the product as a foam.

EXAMPLE NO. 635 Preparation of N-methyl-N'-t-butyl-N,N'-dibenzoylhydrazine

To a stirred solution of N'-t-butyl-N,N'-dibenzoylhydrazine (2.5 g, 0.008 M) in dimethylformamide (DMF) (30 ml) at room temperature under nitrogen was added portionwise sodium hydride (60% oil dispersion) (0.4 g, 0.009 M). The mixture was stirred at room temperature for 0.5 hours, and then methyl iodide (1.0 g, 0.008 M) was added dropwise. The reaction mixture was allowed to stir for 1 hour. The mixture was then diluted with water (50 ml), neutralized with 10% HCl, and the product extracted into methylene chloride (50 ml). The methylene chloride layer was washed with water (5×20 ml), dried over anhydrous magnesium sulfate, and the methylene chloride removed under vacuum to afford N-methyl-N'-t-butyl-N,N'-dibenzoylhydrazine as an oil.

EXAMPLE NO. 636 Preparation of N-benzyl-N'-t-butyl-N,N'-dibenzoylhydrazine

To a stirred solution of N'-t-butyl-N,N'-dibenzoylhydrazine (2 g, 0.006 M) in DMF (25 ml) at room temperature under nitrogen was added portionwise sodium hydride (60% oil dispersion) (0.3 g, 0.007 M). The mixture was stirred at room temperature for 0.5 hours, and then benzyl bromide (1.2 g, 0.007 M) was added dropwise. The reaction mixture was warmed to 60° C. and allowed to stir for 2 hours. The mixture was then diluted with water (50 ml), neutralized with 10% HCl, and the product extracted into methylene chloride (50 ml). The methylene chloride layer was washed with water (5×20 ml), dried over anhydrous magnesium sulfate, and the methylene chloride removed under vacuum to afford N-benzyl-N'-t-butyl-N,N'-dibenzoylhydrazine as an oil.

EXAMPLE NO. 637 Preparation of N-allyl-N'-t-butyl-N,N'-dibenzoylhydrazine

To a stirred solution of N'-t-butyl-N,N'-dibenzoylhydrazine (3 g, 0.011 M) in DMF (30 ml) at room temperature under nitrogen was added portionwise sodium hydride (60% oil dispersion) (0.5 g, 0.012 M). The mixture was stirred at room temperature for 0.5 hours, and then allyl iodide (1.8 g, 0.01 M) was added dropwise. The reaction mixture was warmed to 60° C. and stirred for 2 hours. The mixture was then diluted with water (50 ml), neutralized with 10% HCl, and the product extracted into methylene chloride (50 ml). The methylene chloride layer was washed with water (5×20 ml), dried over anhydrous magnesium sulfate, and the methylene chloride removed under vacuum to afford N-allyl-N'-t-butyl-N,N'-dibenzoylhydrazine as an oil.

EXAMPLE NO. 638 Preparation of N-methoxymethyl-N'-t-butyl-N-N'-dibenzoylhydrazine

N'-t-butyl-N,N'-dibenzoylhydrazine (2 g, 0.007 M) was stirred at room temperature in a two phase system of toluene-50% sodium hydroxide with 100 mg of phase transfer catalyst (tetra-n-butylammonium hydrogen sulfate). Methoxymethyl chloride (1.2 g, 0.015 M) was added dropwise and the mixture was stirred 3 hours. The layers were separated and the toluene layer was washed several times with water (until the water washes were neutral). The toluene solution was dried over anhydrous magnesium sulfate and the toluene removed under vacuum to afford N-methoxymethyl-N'-t-butyl-N,N'-dibenzoylhydrazine as a thick oil.

EXAMPLE NO. 639 Preparation of N-methylthiomethyl-N'-t-butyl-N,N'-dibenzoylhydrazine

To a stirred suspension of sodium hydride (a 50% oil dispersion washed 2 times with 20 ml pentane) (0.21 g, 0.0043 M) in dry DMF (20 ml) under nitrogen at room temperature, was added N'-t-butyl-N,N'-dibenzoylhydrazine (1 g, 0.0034 M) portionwise as a solid. The mixture was stirred at room temperature for 1/2 hour and methylthiomethylchloride (0.34 g, 0.0035M) was added dropwise. The resulting mixture was heated at 50° C. overnight, cooled, diluted with methylene chloride and washed repeatedly with water. The organic layer was dried over anhydrous magnesium sulfate and the methylene chloride removed under vacuum. The oily residue was chromatographed on silica gel using methylene chloride to afford N-methylthiomethyl-N'-t-butyl-N,N'-dibenzoylhydrazine as an oil (60% yield).

EXAMPLE NO. 642 Preparation of N-(2-propynyl)-N'-t-butyl-N-benzoyl-N'-(3,5-dimethylbenzoyl)hydrazine

To a stirred suspension of N'-t-butyl-N-benzoyl-N'-(3,5-dimethylbenzoyl)hydrazine (1.5 g) in dimethylformamide (DMF) (20 ml) was added sodium hydride (200 mg of 60% oil dispersion) portionwise. After 15 min., propargyl bromide (0.6 g) was added to the reaction mixture dropwise and the reaction stirred for 1 hour. The reaction mixture was diluted with ethyl acetate (50 ml) and washed with water (5×20 ml). The organic layer was then dried over magnesium sulfate and the solvent removed under vacuum to afford N-(2-propynyl)-N'-t-butyl-N-benzoyl-N'-(3,5-dimethylbenzoyl)hydrazine as a yellow amorphous solid. The product, N-(2-propynyl)-N'-t-butyl-N-benzoyl-N'-(3,5-dimethylbenzoyl)hydrazine, was purified by column chromatography on silica gel (solvent system:methylene chloride) to afford a 70% yield as a white solid.

EXAMPLE NO. 646 Preparation of N'-t-butyl-N-cyclohexyl-carbonyl-N'-benzoylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (2.0 g, 0.016M) in toluene (30 ml) was added 50% sodium hydroxide (1.3 g, 0.016M). After 15 minutes, the mixture was cooled to 5° C. and cyclohexanecarbonylchloride (2.4 g, 0.016 M) and 50% sodium hydroxide (1.3 g, 0.016M) were added separately and simultaneously so as to maintain the reaction temperature below 10° C. After the addition, the reaction mixture was allowed to warm to room temperature and stirred for 1 hr. The mixture was diluted with hexane and the solid product isolated by filtration. This product (1.5 g, 0.008M) was dissolved in a stirred mixture of toluene (30 ml) and cooled on ice. To this mixture was added benzoylchloride (1.1 g, 0.008 M) and 50% sodium hydroxide (0.6 g, 0.008M) simultaneously. After addition, the mixture was stirred for 1/2 hr., diluted with hexane and the solid product, N'-t-butyl-N-cyclohexylcarbonyl-N'-benzoylhydrazine, isolated by filtration.

EXAMPLE NO. 648 Preparation of N'-t-butyl-N-valeryl-N'-benzoylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (24.8 g, 0.20 mole) in toluene (150 ml) at 5° C. was added one equivalent of NaOH, prepared by diluting 16 g of 50% aqueous (aq.) NaOH to 30 ml. After addition, valeryl chloride (24 g, 0.2 mole) and another one equivalent of NaOH solution (30 ml) were dropwise added separately and simultaneously. The reaction mixture was warmed to room temperature and stirred for 40 min. The two phase mixture was separated and the organic layer was washed with water and brine. The organic layer was dried over Na₂ SO₄ and concentrated under vacuum to give a colorless oil.

To a stirred solution of 1-t-butyl-2-valerylhydrazine (4 g, 0.023M) in toluene (40 ml) at 5° C. was added benzoyl chloride (3.4 g, 0.024 M) and 50% aq. sodium hydroxide (0.98 g, 0.024M). After addition, the mixture was warmed to room temperature and stirred 2.5 hr. The mixture was diluted with ethyl acetate (50 ml) and washed with water (2×25 ml) and brine (1×25 ml). The organic layer was dried over magnesium sulfate and concentrated under vacuum to afford N'-t-butyl-N-valeryl-N'-benzoylhydrazine as a yellow oil.

EXAMPLE NO. 654 Preparation of N'-t-butyl-N-phenyl-acetyl-N'-benzoylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (2.0 g, 0.016M) in toluene (30 ml) was added 50% sodium hydroxide (1.3 g, 0.016M). After 15 minutes, the mixture was cooled to 5° C. and phenylacetyl chloride (2.4 g, 0.016M) and 50% sodium hydroxide (1.3 g, 0.016M) were added separately and simultaneously so as to maintain the reaction temperature below 10° C. After the addition, the reaction mixture was allowed to warm to room temperature and stirred for 1 hr. The mixture was diluted with hexane and the solid product isolated by filtration. This product (3.2 g, 0.015M) was dissolved in a stirred mixture of toluene (30 ml) and cooled on ice. To this mixture was added benzoylchloride (2.2 g, 0.016M) and 50% sodium hydroxide (1.3 g, 0.016M) simultaneously. After addition, the mixture was stirred for 1/2 hr., diluted with hexane and the solid product, N'-t-butyl-N-phenylacetyl-N'-benzoylhydrazine, isolated by filtration.

EXAMPLE NO. 656 Preparation of N'-t-butyl-N-cyclo-hexenylcarbonyl-N'-benzoylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (0.86 g, 0.007M) in toluene (30 ml) was added 50% sodium hydroxide (0.55 g, 0.007M). After 15 minutes, the mixture was cooled to 5° C. and cyclohexenylcarbonyl chloride (1.0 g, 0.007M) and 50% sodium hydroxide (0.55 g, 0.007M) were added separately and simultaneously so as to maintain the reaction temperature below 10° C. After the addition, the reaction mixture was allowed to warm to room temperature and stirred for 1 hr. The mixture was diluted with hexane and the solid product isolated by filtration. This product (1.2 g, 0.006M) was dissolved in toluene (30 ml) and cooled on ice while stirring. To this mixture was added benzoylchloride (1.0 g, 0.007M) and 50% sodium hydroxide (1.3 g, 0.007M) simultaneously. After addition, the mixture was stirred for 1/2 hr., diluted with hexane and the solid product, N'-t-butyl-N-cyclohexenylcarbonyl-N'-benzoylhydrazine, isolated by filtration.

EXAMPLE NO. 659 Preparation of N'-t-butyl-N-(beta-chloropivaloyl)-N'-benzoylhydrazine

To a stirred suspension of tert-butylhydrazine hydrochloride (200 g, 1.61 mole) in acetone (400 ml) was dropwise added triethylamine (200 g, 1.98 mole). After addition, the mixture was refluxed for 3 hours while periodically adding magnesium sulfate (100 g total). The mixture was cooled to room temperature and funnel filtered. The filtrate was dried over magnesium sulfate and concentrated under vacuum at 5° C. until a slurry formed. The mixture was diluted with ethyl acetate (100 ml) and was filtered. The filtrate was distilled yielding a yellow oil (b.p. 121-127° C.).

Into a stirred suspension of 1-t-butyl-2-acetonehydrazone (43 g, 0.34 mole) in toluene (250 ml) at 5° C. was added 10% aq. sodium hydroxide (200 ml, 0.50 mole). After addition, benzoylchloride (70 g, 0.50 mole) was added dropwise to this mixture. Stirring was continued for 2 hours at 5° C. and 72 hours at room temperature. The mixture was diluted with ethyl acetate (300 ml) and washed with water (3×200 ml) and brine (200 ml). The organic layer was dried over magnesium sulfate and concentrated at 35° C. under vacuum to afford a yellow oil.

A mixture of 1-t-butyl-1-benzoyl-2-acetone hydrazone (90 g, approximately 60% pure,approximately 0.3 mole), ethanol (500 ml, 200 proof) and 10% aq. hydrochloric acid (500 ml) was stirred overnight at room temperature. The mixture was concentrated under vacuum to a thick slurry. The slurry was suction filtered with a water wash (400 ml). The solids were air-dried overnight.

The solids were dissolved in a water (200 ml) and methanol (100 ml) solution on a steam bath. The mixture stood at room temperature overnight. The mixture was suction filtered and rinsed with cold water (100 ml) and the solids were air dried overnight. The solids were dissolved in 10% aq. hydrochloric acid (300 ml) and were washed with ethyl acetate (3×300 ml). The ethyl acetate washes were combined and extracted with 10% aq. hydrochloric acid (250 ml). The 10% aq. hydrochloric acid layers were combined and were neutralized with 50% aq. sodium hydroxide while being stirred. Stirring was continued for 1 hour at room temperature. The mixture was suction filtered and rinsed with water (100 ml) and the solids were air-dried yielding a white solid (m.p. 125-126° C.).

To a stirred solution of 1-t-butyl-1-benzoylhydrazine (1 g, 0.005M) in toluene (40 ml) cooled to 5° C. was added 3-chloro-2,2-dimethylpropionylchloride (1.2 g, 0.007M) and 50% aq. sodium hydroxide (0.45 g, 0.0056M) so as to maintain the temperature below 10° C. The mixture was warmed to room temperature and stirred 1 hr. The mixture was diluted with hexane (40 ml) and water (10 ml). The white solid product N'-t-butyl-N-(beta-chloropivaloyl)-N'-benzoylhydrazine was isolated by suction filtration, washed with 50 ml hexane and 50 ml water and dried.

EXAMPLE NO. 661 Preparation of N'-t-butyl-N-(1,2,2-trichlorovinyl)carbonyl-N'-benzoylhydrazine

To a stirred suspension of tert-butylhydrazine hydrochloride (200 g, 1.61 mole) in acetone (400 ml) was dropwise added triethylamine (200 g, 1.98 mole). After addition, the mixture was refluxed for 3 hours while periodically adding magnesium sulfate (100 g total). The mixture was cooled to room temperature and funnel filtered. The filtrate was dried over magnesium sulfate and concentrated under vacuum at 5° C. until a slurry formed. The mixture was diluted with ethylacetate (100 ml) and was filtered. The filtrate was distilled yielding a lightly yellow tinted oil (b.p. 121-127° C.).

To a stirred suspension of 1-t-butyl-2-acetonehydrazone (43 g, 0.34 mole) in toluene (250 ml) at 5° C. was added 10% aq. sodium hydroxide (200 ml, 0.50 mole). After addition, benzoylchloride (70 g, 0.50 mole) was added dropwise to the mixture. Stirring was continued for 2 hours at 5° C. and 72 hours at room temperature. The mixture was diluted with ethyl acetate (300 ml) and washed with water (3×200 ml) and brine (200 ml). The organic layer was dried over magnesium sulfate and concentrated at 35° C. under vacuum yielding a yellow oil.

A mixture of 1-t-butyl-1-benzoyl-2-acetone hydrazone (90 g, approximately 60% pure, approximately 0.3 mole), ethanol (500 ml, 200 proof) and 10% aq. hydrochloric acid (500 ml) was stirred overnight at room temperature. The mixture was concentrated under vacuum to a thick slurry. The slurry was suction filtered and washed with water (400 ml). The solids were air-dried overnight.

The solids were dissolved in a water (200 ml) and methanol (100 ml) solution on a steam bath. The mixture stood at room temperature overnight. The mixture was suction filtered and rinsed with cold water (100 ml) and the solids were air dried overnight. The solids were dissolved in 10% aq. hydrochloric acid (300 ml) and were washed with ethyl acetate (3×300 ml). The ethyl acetate washes were combined and extracted with 10% aq. hydrochloric acid (250 ml). The 10% aq. hydrochloric acid layers were combined and were neutralized with 50% aq. sodium hydroxide while being stirred. Stirring was continued for 1 hour at room temperature. The mixture was suction filtered and rinsed with water (100 ml) and the solids were air-dried yielding a white solid (m.p. 125-126° C.).

To a stirred solution of 1-t-butyl-1-benzoylhydrazine (1.5 g, 0.008 M) in methylene chloride at 5° C. was added, simultaneously and separately, trichloroacryloylchloride (1.7 g, 0.009 M) and triethylamine (0.9 g, 0.009 M). After addition, the reaction was warmed to room temperature and stirred for 3 h. The flask's contents were diluted with 50 ml methylene chloride and washed with water (3×75 ml) and brine solution (1×75 ml). The organic layer was dried over magnesium sulfate and the solvent removed under vacuum to afford N'-t-butyl-N-(1,2,2-trichlorovinyl)carbonyl-N'-benzoylhydrazine as a white solid product.

EXAMPLE 682 Preparation of N'-t-butyl-N-benzoyl-N'-n-pentanecarbonylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (1 g, 0.008M) in toluene (30 ml) at room temperature was added dropwise a 50% aqueous solution of sodium hydroxide (0.64 g, 0.008M). After 15 min., the reaction mixture was cooled to 5° C. and a solution of benzoyl chloride (1.12 g, 0.008M) in toluene (5 ml) and a solution of aqueous 50% sodium hydroxide (0.64 g, 0.008M) were added dropwise simultaneously from separate addition funnels while maintaining the temperature at or below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction was diluted with hexane and the solid N'-t-butyl-N'-benzoylhydrazine was isolated by filtration.

To a stirred solution of the monobenzoylated compound (1.4 g, 0.0073M) in toluene (30 ml) at 5° C., were added dropwise simultaneously from separate addition funnels, solutions of hexanoyl chloride (1 g, 0.0073 M) in toluene (5 ml) and aqueous 50% sodium hydroxide solution (0.58 g, 0.0073 M) while maintaining the temperature below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The mixture was then diluted with hexane and the solid product isolated by filtration. The product was washed with water and hexane and dried. The crude product was recrystallized from ether-methanol to afford N'-t-butyl-N-benzoyl-N'-n-pentanecarbonylhydrazine as a white powder. m.p. 117-118° C.

EXAMPLE 683 Preparation of N'-t-butyl-N-benzoyl-N'-cyclohexanecarbonylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (1 g, 0.008M) in toluene (30 ml) at room temperature was added dropwise a 50% aqueous solution of sodium hydroxide (0.6 g, 0.008M). After 15 min., the reaction mixture was cooled to 5° C. and a solution of benzoyl chloride (1.12 g, 0.008M) in toluene (5 ml) and a solution of aqueous 50% sodium hydroxide (0.64 g, 0.008 M) were added dropwise and simultaneously from separate addition funnels while maintaining the temperature at or below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction was diluted with hexane and the solid N'-t-butyl-N-benzoylhydrazine was isolated by filtration.

To a stirred solution of the monobenzoylated compound (1.4 g, 0.0073M) in toluene (30 ml) at 5° C., were added dropwise and simultaneously from separate addition funnels, solutions of cyclohexanecarbonyl chloride (1.1 g, 0.0073M) in toluene (5 ml) and aqueous 50% sodium hydroxide solution (0.58 g, 0.0073M) while maintaining the temperature below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The mixture was then diluted with hexane and the solid product isolated by filtration. The product was washed with water and hexane and dried. The crude product was recrystallized from ether-methanol to afford N'-t-butyl-N-benzoyl-N'-cyclohexanecarbonylhydrazine as a white powder. m.p. 202-204° C.

EXAMPLE 688 Preparation of N'-t-butyl-N-benzoyl-N'-pivaloylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (2 g, 0.016M) in toluene (50 ml) at room temperature was added dropwise a 50% aqueous solution of sodium hydroxide (1.28 g, 0.016M). After 15 min., the reaction mixture was cooled to 5° C. and a solution of benzoyl chloride (2.3 g, 0.017M) in toluene (5 ml) and a solution of aqueous 50% sodium hydroxide (1.36 g, 0.017M) were added dropwise simultaneously from separate addition funnels while maintaining the temperature at or below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction mixture was diluted with hexane and the solid N'-t-butyl-N-benzoylhydrazine was isolated by filtration.

To a stirred solution of the monobenzoylated compound (2 g, 0.010M) in pyridine (15 ml) was added pivaloyl chloride (1.8 g, 0.015M) and a catalytic amount of 4-dimethylamino pyridine. The mixture was heated to 60° C. and stirred for approximately 1 hr., cooled and diluted with methylene chloride. The organic layer was washed with 10% HCl (3×25 ml) and water (50 ml), dried over magnesium sulfate and the solvent removed under vacuum. The solid product was recrystallized from methanol-ether to afford N'-t-butyl-N-benzoyl-N'-pivaloylhydrazine in 60% yield as a white solid. m.p. 217-220° C.

EXAMPLE 689 Preparation of N'-t-butyl-N-benzoyl-N'-phenylacetylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (1 g, 0.008M) in toluene (30 ml) at room temperature was added dropwise a 50% aqueous solution of sodium hydroxide (0.64 g, 0.008M). After 15 min., the reaction mixture was cooled to 5° C. and a solution of benzoyl chloride (1.12 g, 0.008 M) in toluene (5 ml) and a solution of aqueous 50% sodium hydroxide (0.64 g, 0.008 M) were added dropwise simultaneously from separate addition funnels while maintaining the temperature at or below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction was diluted with hexane and the solid N'-t-butyl-N-benzoylhydrazine was isolated by filtration.

To a stirred solution of the monobenzoylated compound (1.5 g, 0.0078M) in toluene (30 ml) at 5° C., were added dropwise and simultaneously from separate addition funnels, solutions of phenylacetyl chloride (1.2 g, 0.008M) in toluene (5 ml) and aqueous 50% sodium hydroxide solution (0.63 g, 0.0078 M) while maintaining the temperature below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The mixture was then diluted with hexane and the solid product isolated by filtration. The product was washed with water and hexane and dried. The crude product was recrystallized from ether-methanol to afford N'-t-butyl-N-benzoyl-N'-phenylacetylhydrazine as a white powder. m.p. 167-169° C.

EXAMPLE 691 Preparation of N'-t-butyl-N-benzoyl-N'-(beta-trifluoromethylcrotonyl)hydrazine

N'-t-butyl-N-benzoylhydrazine (1.0 g,) in 2 ml toluene was added dropwise to a solution of beta-trifluoromethylcrotonyl chloride (prepared by addition of oxalyl chloride (1.3 g) to a solution of 1.5 g beta-trifluoromethylcrotonic acid in 5 ml toluene at 23° C.). After 30 min. at 23° C., the reaction mixture was partitioned between saturated aqueous sodium bicarbonate (20 ml) and ether (20 ml). The ether layer was evaporated under reduced pressure to about 10 ml and the excess hydrazine was removed by filtration. The filtrate was evaporated to give N'-t-butyl-N-benzoyl-N'-(beta-trifluoromethylcrotonyl)hydrazine as a colorless oil.

EXAMPLE 699 Preparation of N'-t-butyl-N-benzoyl-N'-methacryloylhydrazine

N'-t-butyl-N-benzoylhdyrazine (0.9 g) suspended in 10 ml toluene and 1 ml H₂ O containing 0.3 g 50% sodium hydroxide was treated with 1.2 g of methacryloyl chloride at 23° C. After 18 hours, 5 ml of hexane was added and N'-t-butyl-N-benzoyl-N'-methacryloylhydrazine was collected by filtration. m.p. 148-152° C.

EXAMPLE 702 Preparation of N'-t-butyl-N'-cyclobutane-carbonyl-N-(4-chlorobenzoyl)hydrazine

To a stirred solution of N'-t-butyl-N-(4-chlorobenzoyl)hydrazine (2.0 g, 8.8 mmole) in toluene (35 ml) at 5° C. was added cyclobutanecarboxylic acid chloride (1.25 g, 10.5 mmole) in one portion. To the above mixture was dropwise added 50% NaOH solution (0.85 g, 10.6 mmole). After addition, the ice water bath was removed and the reaction mixture was stirred at room temperature overnight.

The mixture was diluted with hexane (30 ml) and H₂ O (30 ml) and stirred for another 30 min. The solid product was collected by suction-filtration and washed with H₂ O (100 ml) and hexane (100 ml) to yield 1.5 g of N'-t-butyl-N'-cyclobutanecarbonyl-N-(4-chlorobenzoyl)hydrazine.

EXAMPLE 722 Preparation of N'-t-butyl-N-benzoyl-N'-isonicotinoylhydrazine

N'-t-butyl-N-benzoylhydrazine (1.0 g, 0.0052 mol) was suspended in 20 ml of toluene. Isonicotinoyl chloride hydrochloride (0.93 g, 0.0052 mol) was added and then a solution of sodium hydroxide (1.25 g of 50% aqueous NaOH) in 5 ml of water was added dropwise. After stirring at 23° C. for 2 hours, the solids were removed by filtration, washed with water and dried in air. The crude product was chromatographed on silica gel using 5% methanol/methylene chloride as eluant to afford pure N'-t-butyl-N-benzoyl-N'-isonicotinoylhydrazine. m.p. >210° C.

EXAMPLE 723 Preparation of N'-t-butyl-N-(2-pyridine-carbonyl)-N'-benzoylhydrazine

A solution of N'-t-butyl-N-(2-pyridinecarbonyl)-hydrazine (1.0 g, 0.00518 mol) in 20 ml of toluene at 23° C. was treated sequentially with 50% sodium hydroxide (1.3 g) and benzoyl chloride (0.728 g). The mixture was stirred overnight. The solids were removed by filtration and washed with water to afford N'-t-butyl-N-(2-pyridinecarbonyl)-N'-benzoylhydrazine.

EXAMPLE 724 Preparation of N'-t-butyl-N-benzoyl-N'-nicotinoylhydrazine

A solution of N'-t-butyl-N-benzoylhydrazine (2.0 g) and nicotinoyl chloride hydrochloride in 20 ml of methylene chloride at 23° C. was treated dropwise with triethylamine (4 ml). The reaction mixture was stirred at 23° C. for 0.5 hours. Solids were removed by filtration. The filtrate was diluted with 10N HCl and ether. The layers were separated and the organic layer was washed with 10N HCl. The aqueous layer was neutralized with solid sodium bicarbonate and extracted with ether. The ether extracts were treated with charcoal and then dried with magnesium sulfate. Evaporation of solvents afforded a yellow oil which was chromatographed on silica gel using as eluant a mixture of 10% CH₃ OH, 40% CH₂ Cl₂, 50% Et₂ O to afford N'-t-butyl-N-benzoyl-N'-nicotinoylhydrazine as a yellow foam. m.p. 60-63° C.

EXAMPLE 727 Preparation of N'-t-butyl-N-(2-pyridinecarbonyl)-N'-(2-nitrobenzoyl)hydrazine

A solution of N'-t-butyl-N-(2-pyridinecarbonyl)-hydrazine (1.0 g, 0.00518 mol) in 20 ml of toluene was treated dropwise simultaneously with a solution of sodium hydroxide (1.24 g of 50% aqueous solution) in 5 ml of water and 2-nitrobenzoyl chloride (0.96 g). The resulting mixture was stirred at 23° C. overnight. Water was added and the mixture was extracted with ether. A second extraction was performed with methylene chloride and the combined organic extracts were dried over magnesium sulfate. Evaporation afforded 0.4 g of N'-t-butyl-N-(2-pyridinecarbonyl)-N'-(2-nitrobenzoyl)hydrazine as a yellow solid. m.p. 137-140° C.

EXAMPLE 729 Preparation of N'-t-butyl-N-(2-pyridine-carbonyl)-N'-(2-bromobenzoyl)hydrazine

An aqueous solution of sodium hydroxide (1.24 g of 50% NaOH diluted with 5 ml of water) was added to a solution of N'-t-butyl-N-(2-pyridinecarbonyl)hydrazine (1.0 g, 0.00518 mol) in 20 ml of toluene at 23° C. The mixture was cooled and treated with 2-bromobenzoyl chloride (1.137 g, 0.00518 mol). The mixture was then stirred at 23° C. overnight. The solids were removed by filtration, washed with water and dried to afford 0.96 g of N'-t-butyl-N-(2-pyridinecarbonyl)-N'-(2-bromobenzoyl)hydrazine as a white solid. m.p. 179-180° C.

EXAMPLE 733 Preparation of N'-t-butyl-N-(2-pyridine-carbonyl)-N'-(3,4-dichlorobenzoyl)hydrazine

A solution of N'-t-butyl-N-(2-pyridinecarbonyl)-hydrazine (0.5 g) in 10 ml of toluene was treated with 50% sodium hydroxide (0.61 g). 3,4-dichlorobenzoyl chloride (0.6 g) was added and the mixture was stirred rapidly for 4 hours at 23° C. and then was allowed to stand for 48 hours. The solids were removed by filtration and washed with water to afford 0.75 g of N'-t-butyl-N-(2-pyridinecarbonyl)-N'-(3,4-dichlorobenzoyl)hydrazine as a white solid. m.p. 175-178° C.

EXAMPLE 737 Preparation of N'-t-butyl-N-(5-bromo-nicotinoyl-N'-(4-chlorobenzoyl)hydrazine

N'-t-butyl-N'-(4-chlorobenzoyl)hydrazine was prepared substantially according to the procedured for preparing N'-t-butyl-N'-benzoylhydrazine described for Example 220 step 3 except 4-chlorobenzoyl chloride was used in place of benzoyl chloride.

A solution of N'-t-butyl-N'-(4-chlorobenzoyl)-hydrazine (0.5 g, 0.0022 mol) and 5-bromonicotinic acid (0.44 g, 0.0022 mol) in 10 ml of methylene chloride containing triethylamine (0.33 g) was added to a solution of methanesulfonyl chloride (0.25 g, 0.0022 mol) in 10 ml of methylene chloride at 0° C. The resulting mixture was stirred at 23° C. for 2 hours and then was allowed to stand overnight at 23° C. Aqueous sodium bicarbonate was added and the layers were separated. The aqueous layer was re-extracted with methylene chloride. The organic extracts were evaporated to give a yellow solid which was triturated with hexane/methylene chloride to afford N'-t-butyl-N-(5-bromonicotinoyl)-N'-(4-chlorobenzoyl)hydrazine as an off-white solid. m.p. 193-197° C.

EXAMPLE 738 Preparation of N'-t-butyl-N-(pyrazine-carbonyl)-N'-benzoylhydrazine

To a mechanically stirred solution of t-butylhydrazine hydrochloride (51 g, 0.41 mol) in dioxane (100 ml) and water (50 ml), cooled in an ice bath was treated with 50% sodium hydroxide (32 g). The resulting mixture was treated dropwise with di-t-butyl-dicarbonate (92 g, 0.42 mol) over about one-half of an hour. After complete addition, the reaction mixture was warmed to room temperature and stirred for 2 hours. The resulting white solid was filtered off, washed with water and air-dried to afford 74 g of N'-t-butyl-N-t-butoxycarbonylhydrazine, mp. 69-71° C.

A mechanically stirred solution of N'-t-butyl-N-t-butoxycarbonylhydrazine (61 g, 0.32 mol) in toluene (120 ml) cooled in an ice bath, was treated dropwise and simultaneously with 50% sodium hydroxide (31 g) in water (50 ml) and benzoyl chloride (45 g). The addition was complete in 20 minutes and the resulting mixture was warmed to room temperature and allowed to stir for one hour. The resulting white solid was filtered, washed with water and air dried to afford 94 g of N-t-butoxycarbonyl-N'-benzoyl-N'-t-butylhydrazine, mp. 167-170° C.

To a mechanically stirred solution of N-t-butoxycarbonyl-N'-benzoyl-N'-t-butylhydrazine (52 g, 0.18 mol) in methanol (100 ml) was added concentrated hydrochloric acid (35 ml). The resulting mixture was stirred at room temperature for 4 days and then neutralized with saturated aqueous sodium bicarbonate. The resulting white solid was filtered, washed with water and dried under vacuum to afford N'-t-butyl-N'-benzoylhydrazine (39 g) mp. 124-125° C.

Triethylamine (1.0 g, 0.01 mol) was added to a solution of N'-t-butyl-N'-benzoylhydrazine (0.86 g, 0.0031 mol) and pyrazine carboxylic acid (0.56 g, 0.0045 mol) in 10 ml of methylene chloride at 23° C. This mixture was added to a solution of methanesulfonyl chloride (0.6 g, 0.0052 mol) in 10 ml of methylene chloride at 0° C. The mixture was stirred at 23° C. for 3 hours and then allowed to stand at 23° C. overnight. Aqueous sodium bicarbonate was added and the layers were separated. The organic extracts were evaporated to give crude product which was triturated with ether to afford N'-t-butyl-N-(pyrazinecarbonyl)-N'-benzoylhydrazine as a white solid. m.p. 181-183° C.

EXAMPLE 739 Preparation of N'-t-butyl-N-isonicotinoyl-N'-benzoylhydrazine

A solution of N'-t-butyl-N'-benzoylhydrazine (0.5 g, 0.00026 mol) in 10 ml of toluene was treated with 50% sodium hydroxide (0.6 g) followed by isonicotinyl chloride hydrochloride (0.47 g, 0.0026 mol). The mixture was stirred at 23° C. overnight. The solids were removed by filtration and washed with water followed by ether to afford N'-t-butyl-N-isonicotinyl-N'-benzoylhydrazine.

EXAMPLE 743 Preparation of N'-t-butyl-N-(2-pyridine-carbonyl)-N'-(4-fluorobenzoyl)hydrazine)

By substantially following the procedures described above for Example 2, except using 4-fluorobenzoyl chloride rather than benzoyl chloride, N'-t-butyl-N-(2-pyridinecarbonyl)-N'-(4-fluorobenzoyl)hydrazine was afforded.

EXAMPLES 754 AND 755 Preparation of N'-t-butyl-N'-(2-pyridinecarbonyl)-N-benzoylhydrazine

To a suspension of 2-picolinic acid (12.8 g, 0.104 mol.) in methylene chloride (80 ml) were added dropwise triethylamine (14 g, 0.139 mol.) in 10 ml methylene chloride followed by methanesulfonyl chloride (13 g, 0.113 mol.) in 10 ml methylene chloride at 0° C. The resulting mixture was stirred for half an hour before the dropwise addition of N'-t-butyl-N-benzoylhydrazine (20.0 g, 0.10 mole) in 80 ml methylene chloride at 0° C. to 23° C. The final dark brown mixture was allowed to stir at 23° C. for one hour, and to stand at 23° C. overnight.

Aqueous sodium bicarbonate was added and the layers were separated. The aqueous layer was re-extracted with methylene chloride. The organic extracts were combined, and dried over magnesium sulfate. Evaporation under reduced pressure gave 25 g of a light green, brown solid. Recrystalization on a steam bath with ethyl acetate:hexane (80:20 v/v) afforded a light yellow solid.

Column chromatography on silica gel, eluted first with methylene chloride and ether and then with ethyl acetate afforded two separate isomers of N'-t-butyl-N'-(2-pyridinecarbonyl)-N-benzoylhydrazine.

EXAMPLE 764 Preparation of N'-t-butyl-N-benzoyl-N'-(2-furoyl)hydrazine

N'-t-butyl-N-benzoylhydrazine (1 g) was dissolved in 20 ml toluene. Water (5 ml) and 50% aqueous sodium hydroxide (1.25 g) was added followed by 2-furoylchloride (0.68 g). After stirring for 7 hours at room temperature, 0.3 g 2-furoylchloride was added. and the mixture stirred for a further 6 hours. The solid product, N'-t-butyl-N-benzoyl-N'-(2-furoyl)hydrazine, was removed by filtration and washed with water. m.p. 155-175° C.

EXAMPLE 765 Preparation of N'-t-butyl-N-benzoyl-N'-(2-thiophenecarbonyl)hydrazine

N'-t-butyl-N-benzoylhydrazine (1.0 g) was dissolved in 20 ml toluene. 50% aqueous sodium hydroxide (1.25 g) was added followed by 2-thiophene-carbonylchloride (0.76 g). The mixture was stirred at room temperature for 14 hours. The solid product, N'-t-butyl-N-benzoyl-N'-(2-thiophenecarbonyl)hydrazine, was removed by filtration and washed with water. m.p. >200° C.

EXAMPLE 766 Preparation of N'-t-butyl-N-(2-thiophene-carbonyl)-N'-benzoylhydrazine

N'-t-butyl-N-(2-thiophenecarbonyl)hydrazine (1 g) was dissolved in 10 ml toluene and treated with 50% aqueous sodium hydroxide (1.0 g) and water (2 ml) followed by benzoylchloride (0.8 g). After stirring for 14 hours at room temperature, the solid product, N'-t-butyl-N-(2-thiophenecarbonyl)-N'-benzoylhydrazine, was removed by filtration and washed with water. m.p. >190° C.

EXAMPLE 767 Preparation of N'-t-butyl-N-(2-furoyl)-N'-benzoylhydrazine

N'-t-butyl-N-(2-furoyl)hydrazine (1.0 g) was dissolved in 10 ml toluene and 2 ml water. 50% aqueous sodium hydroxide (1.0 g) was added followed by benzoylchloride (0.8 g). After stirring for 14 hours at room temperature, the solid product, N'-t-butyl-N-(2-furoyl)-N'-benzoylhydrazine, was removed by filtration and washed with water. m.p. 160-162° C.

EXAMPLE 772 Preparation of N'-t-butyl-N-(4-methyl-benzoyl)-N'-(2,5-dichlorothiophene-3-carbonyl)-hydrazine

N'-t-butyl-N-4-methylbenzoylhydrazine (0.7 g) was dissolved in 35 ml toluene. Water (5 ml) and 50% aqueous sodium hydroxide (0.8 g) were added followed by 2,5-dichlorothiophene-3-carbonylchloride (2.0 g). After stirring for 3 hours at room temperature, ether was added and the organic layer separated. Evaporation afforded a solid which was triturated with 10% ether-hexane to afford N'-t-butyl-N-(4-methylbenzoyl)-N'-(2,5-dichlorothiophene-3-carbonyl)hydrazine. m.p. 163-165° C.

EXAMPLE 778 Preparation of N'-t-butyl-N-(N-methyl-2-pyrrolecarbonyl)-N'-benzoylhydrazine

N'-t-butyl-N-(N-methyl-2-carbonylpyrrole)hydrazine (0.8 g) was dissolved in 10 ml toluene and 1 ml water. 50% aqueous sodium hydroxide (10 drops) was added followed by benzoylchloride (1.2 g). After 14 hours stirring at room temperature, ether was added and the product, N'-t-butyl-N-(N-methyl-2-pyrrolecarbonyl)-N'-benzoylhydrazine, was isolated by filtration and washed with ether. m.p. 182-185° C.

EXAMPLE 787 Preparation of N'-t-butyl-N-(1,2,3-triazole-4-carbonyl)-N'-(3-methylbenzoyl)hydrazine

1,2,3-triazole-4-carboxylic acid (1.0 g) and triethylamine (0.9 g) were dissolved in 40 ml methylene chloride and cooled in an ice bath. Methanesulfonylchloride (1.0 g) was added dropwise. After addition was complete, the reaction mixture was stirred for 0.5 hours. N'-t-butyl-N'-(3-methylbenzoyl)hydrazine (1.84 g) in 10 ml CH₂ Cl₂ was added dropwise. The resulting mixture was allowed to stand for 14 hours. Aqueous sodium bicarbonate was added. The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated to give a yellow oil. Chromatography on silica gel using acetone as eluant afforded N'-t-butyl-N-1,2,3-triazole-4-carbonyl-N'-(3-methylbenzoyl)hydrazine.

EXAMPLE 802 Preparation of N'-(1-cyano-1-methyl-)ethyl-N,N'-dibenzoylhydrazine

To a suspension of benzoylhydrazine (13.6 g, 0.1 mole) in deionized water (50 ml) at 5° C. with stirring was dropwise added concentrated hydrogen chloride (9.8 g, 0.1 mole). To the resulting clear solution was added sodium cyanide (5.2 g, 0.1 mole) and acetone (6.5 g, 0.11 mole). A white and thick precipitate appeared. The cooling bath was removed and the reaction flask was stoppered tightly. The reaction mixture was stirred for 18 hours. The precipitate was collected by suction-filtration and was washed with a small amount of water to give 17.5 g (86.2% yielded) of the desired intermediate, N'-(1-cyano-1-methyl)ethyl-N-benzoic acid hydrazide, as the starting material for the next step. (m.p. 82-92° C.)

To the solution of N'-(1-cyano-1-methyl)ethyl-N-benzoic acid hydrazide (2 g, 0.01 mole) in dry methylene chloride (25 ml) under nitrogen at room temperature with stirring was added benzoyl chloride (2.02 g, 0.014 mole). To the above mixture was dropwise added triethylamine (1.31 g, 0.013 mole). The reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with methylene chloride (50 ml), washed with water and brine. The organic layer was dried over MgSO₄ and the solvent was evaporated at reduced pressure to give a residue. The residue was treated with ethyl acetate/hexane mixture (1:1) affording a crude solid product which was collected by suction-filtration (1 g, 33% yield). An analytical sample was obtained by crystallization from ethyl acetate/hexane (4:1), m.p. 202-204° C. NMR and IR spectra showed the desired product.

EXAMPLE 809 Preparation of N'-(1-cyano-1-methyl-)ethyl-N,N'-di-4-tolylhydrazine

To the suspension of 4-toluic acid hydrazide (15.0 g, 0.1 mole) in water (150 ml) and ethanol (20 ml) at 5° C. with stirring was dropwise added concentrated hydrogen chloride (10 g, 0.1 mole). To the above suspension was carefully added sodium cyanide (5.3 g, 0.1 mole) and acetone (6.6 g, 0.11 mole). The reaction flask was stoppered tightly and the cooling bath was removed. The resulting viscous reaction mixture was stirred at room temperature for more than 24 hours. The precipitate was collected by suction-filtration and was washed with a small amount of diluted hydrogen chloride and water affording 14.6 g. (64.8%) of N'-(1-cyano-1-methyl)ethyl-4-toluic acid hydrazide as the starting material for the next step. Analytical sample was obtained by crystallization from ethyl acetate/hexane (3:1), m.p. 146-148° C.

To the solution of N'-(1-cyano-1-methyl)ethyl-4-toluic acid hydrazide (2.17 g, 0.01 mole) in dry methylene chloride (65 ml) under nitrogen with magnetic stirring was added 4-dimethylaminopyridine catalyst (1.34 g, 0.011 mole) followed by 4-methylbenzoyl chloride (2.52 g, 0.017 mole). To the above mixture was dropwise added triethylamine (1.1 g, 0.011 mole). The reaction mixture was slightly exothermic. After stirring at room temperature for 40 minutes the reaction mixture was diluted with methylene chloride (50 ml), washed with diluted HCl solution (2×50 ml), dil NaOH (50 ml), H₂ O (50 ml) and brine. The organic layer was dried over MgSO₄, and the solvent was evaporated under reduced pressure to give a residue. The residue was treated with ethyl acetate/hexane mixture (1:1) and the resulting solid was collected by suction-filtration and affording 2.75 g (82% yield) of almost pure product. (m.p. 192-198° C.) NMR and IR spectra showed the desired product.

EXAMPLE NO. 822 Preparation of N'-(1,1-dimethyl-3-butenyl)-N,N'dibenzoylhydrazine

To a gently refluxing solution of allyl magnesium bromide (380 ml of 1M solution) was added acetone azine (20 g) dissolved in diethyl ether (200 ml). The solution was refluxed for three days. Upon cooling, a saturated solution of ammonium chloride (50 ml) was added. The aqueous layer was separated and washed twice with diethyl ether (200 ml). The combined ether extracts were dried over anhydrous magnesium sulfate, filtered and the ether removed at reduced pressure. The product was distilled through a vigreux column at 3.1 torr and collected in a dry ice/acetone cooled receiving flask. The boiling point was 60-65° C. 15 g of product was collected.

Oxalic acid (16.7 g) was dissolved in a solution of ethanol:diethyl ether (1:1) (150 ml) and water (3.3 g) was added. To this acid solution was added the hydrazone (13 g) dissolved in diethyl ether (75 ml). The solution was stirred for 24 hours then filtered. The solid is washed once with diethyl ether. The filtrate was concentrated and combined with the solid to afford a 71% yield (17.2 g) of the hydrazine oxalate.

The 1,1-dimethyl-3-butenylhydrazine oxalate (2 g) was dissolved in toluene and neutralized with 50% aqueous sodium hydroxide. To this solution was added benzoyl chloride (2.8 g) and sodium hydroxide (50% Aq. solution) (3.2 g) at 25° C. The reaction mixture was warmed to room temperature and stirred. The mixture was diluted with hexane and filtered to afford an oily product which solidified upon standing. (m.p. 105-112° C.)

EXAMPLE NO. 829 Preparation of N'-t-butyl-N-benzoyl-N'-benzylhydrazine

Benzyl bromide (0.9 g), 1-benzoyl-2-t-butyl hydrazine (1 g) and triethylamine (0.52 g) were warmed in dimethylformamide (50 ml) at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, diluted with diethylether (100 ml) and washed three times with 25 ml of water. The organic layer was dried over magnesium sulfate, filtered, and the solvent removed in vacuo to afford the product as a white solid. The product was chromatographed on silica gel (G:70 to 230 mesh) using methylene chloride as eluent to afford a 75% yield of a white solid: m.p. 147-149.

EXAMPLE NO. 837 Preparation of N'-t-butyl-N-furoyl-N'-benzylhydrazine

Benzyl bromide (1.8 g), 1-furoyl-2-t-butyl hydrazine (2 g) and excess powdered potassium carbonate were stirred in dimethylformamide (50 ml) at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, diluted with diethyl ether and washed several times with water. The organic layer was dried over magnesium sulfate, filtered, and the solvent removed in vacuo. The white solid product was chromatographed on silica gel (G:70-230 mesh) using methylene chloride as eluent to afford the product in good yield: m.p. 152-153.

EXAMPLE NO. 853 Preparation of N'-t-butyl-N-benzoyl-N'-methylpyridinylhydrazine

N'-t-butyl-N-benzoyl hydrazine (1.2 g), 2-chloromethyl pyridine (1.0 g) and triethylamine (2 equivalents) were stirred in dimethyl sulfoxide (15 ml) at room temperature for 2 hours. The reaction mixture was then warmed to 50° C. for 2 hours. The mixture was diluted with ether and washed with water. The organic layer was dried over magnesium sulfate, filtered and rotavapped to afford a yellow oil. The oil was chromatographed on silica gel (G:70-230 mesh) using a methylene chloride-ether mixture (1:1) as eluent to afford the purified product as a yellow gum in approximately 20% yield.

EXAMPLE NO. 855 Preparation of N'-t-butyl-N-benzyl-N'-benzoylhydrazine

N'-t-butyl-N'-benzoyl benzaldehyde hydrazone (1.8 g) and sodium cyanoborohydride (1.5 equivalents) were stirred in dry methanol (30 ml) at room temperature. Ten percent HCl was added to bring the pH of the reaction mixture to pH 3-4 and stirred at room temperature for 1 hour. The methanol was removed in vacuo and the residue was dissolved in methylene chloride. The methylene chloride layer was washed with saturated aqueous sodium bicarbonate and then with water. The organic layer was dried over magnesium sulfate, filtered and the solvent removed in vacuo to afford in good yield a white solid: m.p. 110-115.

EXAMPLE NO. 864 Preparation of N'-t-butyl-N'-benzoyl-benzaldehyde hydrazone

Benzaldehyde (10.6 g), t-butylhydrazine, hydrochloride (12.4 g) and triethylamine (10.1 g) were stirred in toluene (150 ml) at room temperature. The reaction mixture was washed with water and dried over magnesium sulfate. The mixture was filtered and the solvent was removed in vacuo to afford N'-t-butyl benzaldehyde hydrazone as a yellow oil in good yield.

The N'-t-butyl benzaldehyde hydrazone (1.76 g) and benzoyl chloride (1.4 g) were stirred in a pyridine-methylene chloride solvent system (1:1, 50 ml), diluted with methylene chloride and washed several times with 10% HCl. The organic layer was dried over magnesium sulfate, filtered and the solvent removed in vacuo to afford a low melting solid in good yield: m.p. 69-72° C.

EXAMPLE NO. 870 Preparation of N-benzoyl-N'-t-butyl-N'-phenylethylhydrazine

N'-t-butyl-N-benzoylhydrazine (2.2 g), powdered potassium carbonate (5 g) and beta-phenethyl bromide (1.8 g) were stirred in dimethylformamide (15 ml) at 60° for 18 hours. The reaction mixture was cooled, and diluted with ether and water. The white solid product was filtered off and recrystallized from ether/hexane to afford 0.3 g of product: m.p. 150-152° C.

EXAMPLE NO. 871 Preparation of N-benzoyl-N'-t-butyl-N'-(ethoxycarbonyl)methylhydrazine

N'-t-butyl-N-benzoylhydrazine (2.0 g), powdered potassium carbonate (5 g) and bromoethyl acetate (1.6 g) were stirred in dimethylformamide (20 ml) at 60° C. for 14 hours. The reaction mixture was diluted with water and ether, and the organic layer was separated. The organic layer was washed several times with water, dried over magnesium sulfate and rotavapped to afford an oil. Chromatographic purification gave the pure oil product (0.25 g).

EXAMPLE NO. 872 Preparation of N'-t-butyl-N'-benzoyl-N-[N-(4-tolyl)aminocarbonyl]hydrazine

N't-butyl-N'-benzoylhydrazine (0.8 g) and p-methylphenylisocyanate (0.9 g) were stirred in diethylether (10 ml) at 23° C. for 15 hours. The reaction mixture was diluted with ether and filtered to afford 0.5 g of solid product: m.p. 208-210° C.

EXAMPLE NO. 873 Preparation of N'-t-butyl-N'-benzoyl-carbonyl-N-benzoylhydrazine

N'-t-butyl-N'-benzoylhydrazine (1 g), benzoyl formic acid (0.7 g) and methanesulfonyl chloride (0.7 g) were stirred in toluene (30 ml) and saturated sodium bicarbonate (10 ml) at approximately 5° C. Triethylamine was added slowly, dropwise to the reaction mixture and stirred 1 hour at room temperature. After stirring for 1 hour, the reaction mixture was diluted with toluene (25 ml) and washed with water several times. The organic layers were dried over magnesium sulfate, filtered and the toluene rotavapped off to afford a white solid. After column chromatography, the product was obtained as a white solid in approximately 70% yield.

EXAMPLE NO. 878 Preparation of N'-t-butyl-N-benzoyl-carbonyl-N'-benzoylhydrazine

N'-t-butyl-N-benzoylhydrazine (1 g), benzoyl formic acid (1 g), and methanesulfonyl chloride (0.7 g) were stirred in toluene (35 ml) and saturated sodium bicarbonate (15 ml) at approximately 5° C. Triethylamine was added slowly, dropwise to the reaction mixture, and slowly warmed to room temperature. After stirring for 1 hour, the reaction mixture was diluted with toluene (20 ml) and the organic layer was washed several times with water. The organic layers were dried over magnesium sulfate, filtered and the toluene rotavapped off to afford a white gum. The crude product was chromatographed on silica gel (G:230-400 mesh) using a methylene chloride ether solvent system as eluent to afford a 65% yield of a white solid.

EXAMPLE NO. 880 Preparation of N'-t-butyl-N-(1,2,3,4-tetrahydronaphthyl-2-carbonyl)-N'-(3-toluoyl)hydrazine

To a stirred suspension of N'-t-butyl-N'-(3-toluoyl)hydrazine (1.2 g) in toluene (10 ml) and aqueous sodium hydroxide (3 ml of 50% solution) was added 1,2,3,4-tetrahydronaphthyl-2-carbonyl chloride (0.007 mol). After stirring 1 hour, hexane and ether were added and the solids filtered off and dried by vacuum oven at 45° C.

EXAMPLE NO. 882 Preparation of N'-t-butyl-N-benzoyl-N'-(alpha-chlorophenylacetylhydrazine)

N'-t-butyl-N-benzoylhydrazine (10 g) was stirred in toluene (100 ml) and saturated sodium bicarbonate (50 ml) at approximately 5-10° C. Alpha-chlorophenylacetylchloride (9.8 g) in toluene (20 ml) was added slowly, dropwise to the cooled reaction mixture, warmed to room temperature and stirred several hours. Hexane (100 ml) was added to the reaction mixture and the solid product was filtered. The filter cake was washed several times with hexane and then water. The product was air dried to afford a 92% yield.

EXAMPLE NO. 883 Preparation of N'-t-butyl-N-benzoyl-N'-phenylacetylhydrazine

N'-t-butyl-N-benzoylhydrazine (2 g) was stirred in toluene (35 ml) and 50% aqueous sodium hydroxide (1 g) at 5° C. Phenylacetylchloride (1.5 g) was added slowly, dropwise to the reaction mixture, warmed to room temperature and stirred 1 hour. The reaction mixture was diluted with hexane (50 ml) and filtered off to yield a solid product. The filter cake was washed with hexane and water and allowed to air dry. The white solid product obtained in 90% yield melted at 167-169° C.

EXAMPLE NO. 893 Preparation of N'-t-butyl-N'-benzoyl-alpha-furoyloxybenzaldehyde hydrazone

N'-benzoyl-N'-t-butyl hydrazine (1.5 g) was stirred in a two-phase solvent system consisting of toluene (20 ml) and 50% aqueous sodium hydroxide (10 ml). First, a phase transfer catalyst, (n-Bu)₄ N+-I (25-50 mg) was added and then 2-furoyl chloride was added dropwise. After the addition, the suspended white solid hydrazine went slowly into solution as it reacted to form the acylated product. After stirring at room temperature for 1 hour, the reaction mixture was diluted with 35 ml water and 30 ml of ethyl acetate. The layers were separated and the organic layer was washed several times with water, dried over magnesium sulfate, filtered and concentrated in vacuo to afford the product as a clear oil. The product was chromatographed on silica gel (G:230-400 mesh) using methylene chloride as the eluting solvent affording a clear, colorless oil (85% yield).

EXAMPLE NO. 905 Preparation of N'-t-butyl-N'-2,4-dichlorobenzoyl-alpha-methoxy-2,3-dimethylbenzaldehyde hydrazone

To a stirred solution of N'-t-butyl-N-(2,3-dimethylbenzoyl)hydrazine (4.2 g) and triphenylphosphine (5.5 g) in dry acetonitrile (60 ml) at room temperature under nitrogen was dropwise added carbon tetrachloride (3.5 g). The reaction mixture was stirred overnight at room temperature. The acetonitrile was removed in vacuo and the crude reaction mixture was chromatographed on silica gel (6, 230-400 mesh) using hexane/ethyl acetate (3:1) to afford the corresponding hydrazinoyl chloride as a yellow oil.

To a stirred suspension of powdered potassium carbonate (2 g) in methanol (75 ml) was added dropwise a solution of the above hydrazinoyl chloride (2.2 g) in methanol (40 ml). The reaction mixture was stirred overnight at room temperature, concentrated in vacuo and the carbonate was filtered off. The filtrate was rotavapped to afford methoxyhydrazine as a while solid (1.9 g).

To a stirred solution of the methoxyhydrazine (1.5 g) in toluene (25 ml) and 50% sodium hydroxide (2 g diluted with 8 g of water) was added 2,4-dichlorobenzoyl chloride (2.5 g) dropwise while the reaction mixture was kept at approximately 0° C. After warming to room temperature, the reaction mixture was diluted with ether and the layers separated. The organic layer was washed twice with water, once with saturated sodium chloride solution and dried over sodium sulfate. Concentration of the reaction gave a product which was chromatographed on silica gel (6, 230-400 mesh) using a hexane/ethyl acetate (4:1) solvent system.

EXAMPLE NO. 914 Preparation of N'-t-butyl-N-benzene-sulfonyl-N'-benzoylhydrazine

N'-t-butyl-N'-benzoylhydrazine (0.4 g) was stirred in pyridine (3 ml) at room temperature. Benzenesulfonyl chloride (0.5 g) was added slowly, dropwise and stirred for 2 hours, diluted with diethyl ether (20 ml) and washed several times with a 10% HCl solution and then water. The organic layer was dried over magnesium sulfate, filtered and the solvent rotavapped off to afford a white solid in good yield.

EXAMPLE NO. 918 Preparation of N'-t-butyl-N-benzoyl-N'-benzenesulfonylhydrazine

N-benzoyl-N'-t-butyl hydrazine (0.8 g) was stirred in pyridine (2 ml) at room temperature. Benzenesulfonyl chloride (0.8 g) was added slowly dropwise, stirred about 1 hour, diluted with diethyl ether (10 ml) and washed several times with a 10% HCl solution and then water. The organic layer was dried over magnesium sulfate. The mixture was filtered and the solvent rotavapped off to afford a white solid in good yield.

EXAMPLE NO. 922 Preparation of N'-t-butyl-N'-[methyl-(2-chlorophenylamino)phosphinyl]-N-benzoylhydrazine

Methyl dichlorophosphine (1.3 g) in ether (10 ml) and triethylamine (2 ml) were added to a stirred solution of N-benzoyl-N'-t-butyl hydrazine (1.0 g) in methylene chloride (3 ml). After stirring 5 minutes at room temperature, o-chloroaniline was added neat producing a mild exotherm. The reaction was quenched 2 minutes later with water (20 ml) and ether (20 ml), separated and the organic washed with 0.1N HCl, dried over MgSO₄, filtered and rotavapped to a colorless oil weighing 0.5 g.

EXAMPLE NO. 923 Preparation of N'-t-butyl-N-methyl-phenylphosphinyl-N'-benzoylhydrazine

Triethylamine (7 ml) and t-butyl hydrazine.HCl (4 g) were stirred in methylene chloride (20 ml) at about 0° C. To this was added, slowly, methylphenylphosphinyl chloride (0.03 mol). The mixture was stirred at 0° C. for 15 minutes and quenched with a sodium bicarbonate solution. The reaction mixture was extracted with diethyl ether, washed with water and dried over magnesium sulfate. After filtering the drying agent, the solvent was removed in vacuo to afford an oily product which was used directly in the subsequent step.

N'-t-butyl-N-(methylphenyl)phosphinylhydrazine (0.7 g) and triethylamine (3 ml) were stirred in diethyl ether (30 ml) at room temperature. Slowly, dropwise benzoyl chloride (1.2 g) was added to the reaction mixture. After stirring 1 hour at room temperature, the reaction mixture was diluted with hexane and the solid product filtered off. The white solid melted at 175-178° C.

EXAMPLE NO. 933 Preparation of N'-t-butyl-N-(2-phenyl-3-methylpentanoyl)-N'-(3-toluoyl)hydrazine

To a stirred suspension of N'-t-butyl-N'-(3-toluoyl)hydrazine (0.7 g) in toluene (10 ml) and aqueous sodium hydroxide (12 drops of 50% aqueous sodium hydroxide) was added dropwise 2-phenyl-3-methyl-pentanoyl chloride (1.0 g). The reaction mixture was stirred overnight, diluted with hexanes and the solids filtered. The solids were washed with hexane and air dried.

EXAMPLE NO. 941 Preparation of N'-t-butyl-N-phenyl-propiolyl-N'-(3-toluoyl)hydrazine

To a stirred solution of N'-(3-toluoyl)-N'-t-butyl hydrazine (1.0 g) in toluene (15 ml) and aqueous sodium hydroxide was added phenylpropiolyl chloride (0.01 mol) dropwise at room temperature. After stirring the reaction mixture for 3 hours, hexane and ether were added and the solids filtered. The solids were vacuum dried at 60° C.

EXAMPLE NO. 942 Preparation of N'-t-butyl-N-(2,3-di-methylbenzoyl)-N'-phenylpropiolylhydrazine

To a stirred solution of N-(2,3-dimethylbenzoyl)-N'-t-butyl hydrazine (1.0 g) in toluene (15 ml) and aqueous sodium hydroxide was added phenylpropiolyl chloride (0.006 mol) dropwise. After stirring 15 minutes at room temperature, ether and hexane were added and the solid product was filtered off.

EXAMPLE NO. 944 Preparation of N'-t-butyl-N-(3,4-epoxy-cyclohexane carbonyl)-N'-(3-toluoyl)hydrazine

To a stirred solution of N'-t-butyl-N'-(3-toluoyl)hydrazine (20 g) in toluene (150 ml) and aqueous sodium hydroxide at 10° C. was added 3-cyclohexenecarbonyl chloride (14.3 g) dropwise at a rate which maintained the temperature at or below 10° C. After stirring at room temperature for 2 hours, hexane was added and the solids filtered. The filler cake was washed with hexane and water and --N'-(3-toluoyl)hydrazine (2 g) and m-chloroperbenzoic acid (1.1 mol equivalents of 80% material) was stirred in methylene chloride (50 ml) overnight. The reaction mixture was diluted with methylene chloride (50 ml) and washed with saturated aqueous sodium bicarbonate solution (3×25 ml), dried over magnesium sulfate, filtered and rotavapped to afford the white solid epoxide in 78% overall yield.

EXAMPLE 948 Preparation of N'-t-butyl-N-pyrenone-carbonyl-N'-(3-toluoyl)hydrazine

To a stirred suspension of t-butyl hydrazine hydrochloride (0.02 mol) in toluene (20 ml) and aqueous hydroxide (5 ml of 50% solution) at room temperature was added pyrenonecarbonyl chloride (0.01 mol). After stirring the reaction mixture for 20 minutes, ether and hexane were added and the solid product was filtered and washed with water. The solid product (0.5 g) was stirred in toluene (10 ml) and aqueous sodium hydroxide and m-toluoyl chloride (0.8 g) was added dropwise. After stirring for 5 hours, hexane and ether were added and the solid product filtered and air dried.

EXAMPLE NO. 1002 Preparation of 1-t-butyl-1-(3- toluoyl)-4-(4-chlorobenzenesulfonyl)semicarbazide

To a solution of N'-t-butyl-N'-3-toluoyl hydrazine (4.03 g, 0.02 mole) in methylene chloride (25 ml) under nitrogen was added 4-chlorobenzenesulfonyl isocyanate (5 g, 80%, 0.02 mole) at room temperature. The exothermic reaction mixture was stirred at room temperature for 30 minutes. The solvent was evaporated under reduced pressure to give an oil. A precipitate appeared after treating with ether. The pure product was collected by suction-filtration and washed with a small amount of ether affording 4.8 g of 1-t-butyl-1-(3-toluoyl)-4-(4-chlorobenzenesulfonyl)semicarbazide as a white solid. m.p. 184-188° C.

EXAMPLE NO. 1008 Preparation of N'-(1-methyl-1-carbamyl)ethyl-N'-3-toluoyl-N-4-chlorobenzoyl hydrazine

To concentrated hydrochloric acid (10 ml) at 0-5° C. was added N'-(1-methyl-1-cyano)ethyl-N'-3-toluoyl-N-4-chlorobenzoyl hydrazine (0.8 g, 2.25 mmole) in one portion with stirring. After stirring for 40 minutes at a temperature below 20° C., the reaction mixture was diluted with water (50 ml) and hexane (50 ml). The resultant suspension was suction-filtered to give the product, N'-(1-methyl-1-carbamyl)ethyl-N'-3-toluoyl-N-4-chlorobenzoyl hydrazine, as a white solid. m.p. 213-218° C. Yield is 0.5 g (59%).

EXAMPLE NO. 1013 Preparation of N'-t-butyl-N'-3-toluoyl-mucochloric acid hydrazone

To a solution of N'-t-butyl-N'-3-toluoylhydrazine (1.03 g, 5 mmole) in 80% methanol (25 ml) was added mucochloric acid (0.85 g, 5 mmole). The reaction mixture was held at room temperature for 2 hours with occasional shaking. The resultant viscous suspension was suction-filtered and washed with water. After air-drying overnight, the product, N'-t-butyl-3-toluoyl mucochloric acid hydrazone, weighed 1.50 g. m.p. 167-168° C.

EXAMPLE NO. 1015 Preparation of N'-t-butyl N'-3-toluoyl-ethylpyruvate hydrazone

To a solution of N'-t-butyl-N'-3-toluoyl hydrazine (2.06 g, 10 mmole) in methylene chloride (20 ml) and water (20 ml) at room temperature with stirring was added ethylpyruvate (2.4 g, 21 mmole). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture turned to two phases. The aqueous phase was extracted with methylene chloride (2×50 ml) and the extracts were combined with the organic phase. The combined organic solution was washed with water and brine, dried over magnesium sulfate, filtered and evaporated to give a liquid product. The product was further dried in vacuum to give 1.9 g of N'-t-butyl-N'-3-toluoyl ethylpyruvate hydrazone as an oil.

EXAMPLE NO. 1016 Preparation of N'-t-butyl-N'-3-toluoyl-acetone hydrazone

To a solution of t-butyl acetone hydrazone (5 g, 39 mmole) in methylene chloride (50 ml) at 0° C. under nitrogen was added 3-toluoyl chloride (6.1 g, 39 mmole), followed by slowly adding triethylamine (3.94 g, 39 mmole). After the addition the reaction mixture was stirred at between 0-5° C. for one hour. The reaction mixture was diluted with methylene chloride (100 ml) and washed subsequently with water, dilute HCl, water, and brine. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated under a reduced pressure to give a light brown liquid. The desired product, N'-t-butyl-N'-3-toluoyl acetone hydrazone, was obtained (2.45 g) by a vacuum distillation. b.p. 96-104° C. at 0.05 mm Hg.

EXAMPLE NO. 1017 Preparation of N'-t-butyl-N'-3-toluoyl-N-isopropylhydrazine

To a solution of N'-t-butyl-N'-3-toluoyl acetone hydrazone (1.5 g, 6.08 mmole) in methanol (50 ml) at room temperature with stirring was added, in small portions, sodium borocyanohydride (0.5 g, 8 mmole). To the above reaction mixture was added 10% HCl (5 ml) and the mixture stirred for 10 minutes. A white precipitate appeared. To this was added water (50 ml) and dilute NaOH until the solution turned basic. The resultant white solid was collected by suction-filtration and washed with water. The product was further dried in vacuum to give 0.9 g (60%) of N'-t-butyl-N'-3-toluoyl-N-isopropylhydrazine as a fluffy white powder. m.p. 107-109° C.

EXAMPLE NO. 1018 Preparation of N'-t-butyl-N'-benzoyl-N-(1-cyano-1-methyl)ethylhydrazine

To a suspension of N'-t-butyl-N'-benzoyl- hydrazine (1.92 g, 10 mmole) in water (30 ml) at 0-5° C. was added concentrated HCl (1 g, 10 mmole), followed by NaCN (0.52 g, 10.6 mmole) and acetone (0.75 g, 12.9 mmole). After the addition, the reaction flask was stoppered tightly and the reaction mixture was stirred at room temperature for 16 hours. The resultant suspension was suction-filtered and washed with water. The product, N'-t-butyl-N'-benzoyl-N-(1-cyano-1-methyl)ethylhydrazine, was further dried in vacuum to give 2.1 g as a white powder. m.p. 117-120° C.

By following substantially the procedures in Examples 1 and 3 and using the reactants shown below in Table II the products of Example Nos. 2, 4 through 12, 14, 19, 20, 32, 37, 55, 98 through 101, 145, 169, 174, 181, 234, 250, 260, 264, 289, 295, 298, 308, 364, 390, 391, 394, 449, 613, 632, 924 through 928, 937, 938, 939, 943, 949, 950, 951, 954, 959, 961, 963, 964, 965, 967, 968, 990 and 996 were prepared.

                  TABLE II                                                         ______________________________________                                         Ex.  Compound of   Compound of                                                   No. Formula III or VI Formula IV Base Solvents                               ______________________________________                                          3   3-chlorobenzoyl                                                                              t-butylhydrazine                                                                           sodium toluene                                     chloride hydrochloride hydroxide and water                                  butylhydrazine sodium toluene                                                     chloride hydrochloride hydroxide and water                                  butylhydrazine sodium toluene                                                     chloride hydrochloride hydroxide and water                                  butylhydrazine sodium toluene                                                     chloride hydrochloride hydroxide and water                                  butylhydrazine sodium toluene                                                     chloride hydrochloride hydroxide and water                                  butylhydrazine sodium toluene                                                     chloride hydrochloride hydroxide and water                                  butylhydrazine sodium toluene                                                     chloride hydrochloride hydroxide and water                                  butylhydrazine sodium toluene                                                     chloride hydrochloride hydroxide and water                                  butylhydrazine sodium toluene                                                     chloride hydrochloride hydroxide and water                                  butylhydrazine sodium toluene                                                     chloride hydrochloride hydroxide and water                                  butylhydrazine sodium toluene                                                     chloride hydrochloride hydroxide and water                                  butylhydrazine sodium toluene                                                     chloride hydrochloride hydroxide and water                                  butylhydrazine sodium toluene                                                     chloride hydrochloride hydroxide and water                                  butylbenzoyl t-butylhydrazine sodium toluene                                      chloride hydrochloride hydroxide and water                                  butylhydrazine sodium toluene                                                     chloride hydrochloride hydroxide and water                                  butylhydrazine sodium toluene                                                      hydrochloride hydroxide and water                                          butylhydrazine sodium toluene                                                     chloride hydrochloride hydroxide and water                                  butylhydrazine sodium toluene                                                     chloride hydrochloride hydroxide and water                                    100 2-fluorobenzoyl t-butylhydrazine sodium toluene                             chloride hydrochloride hydroxide and water                                    101 2-naphthoylchloride t-butylhydrazine sodium toluene                          hydrochloride hydroxide and water                                            145 4-biphenylbenzoyl t-butylhydrazine sodium toluene                           chloride hydrochloride hydroxide and water                                    169 2-chloromethyl- t-butylhydrazine sodium toluene                             benzoyl chloride hydrochloride hydroxide and water                            174 2-bromobenzoyl t-butylhydrazine sodium toluene                              chloride hydrochloride hydroxide and water                                    181 4-ethylbenzoyl t-butylhydrazine sodium toluene                              chloride hydrochloride hydroxide and water                                    234 3-methoxy benzoyl t-butylhydrazine sodium toluene                           chloride hydrochloride hydroxide and water                                    250 benzoyl chloride 2,2-dimethyl- sodium toluene                                pentylhydrazine hydroxide and water                                            oxalic acid salt                                                             260 2-nitro-4-chloro- t-butylhydrazine sodium toluene                           benzoyl chloride hydrochloride hydroxide and water                            264 2,6-difluorobenzoyl t-butylhydrazine sodium toluene                         chloride hydrochloride hydroxide and water                                    289 4-vinylbenzoyl t-butylhydrazine sodium toluene                              chloride hydrochloride hydroxide and water                                    295 benzoyl chloride 2,2-dimethyl- sodium toluene                                propylhydrazine hydroxide and water                                            oxalic acid salt                                                             298 2-bromobenzoyl 2,2-dimethyl- sodium toluene                                 chloride propylhydrazine hydroxide and water                                    oxalic acid salt                                                             308 4-(1-propenyl)- t-butylhydrazine sodium toluene                             benzoyl chloride hydrochloride hydroxide and water                            364 4-bromobenzoyl t-butylhydrazine sodium toluene                              chloride hydrochloride hydroxide and water                                    390 3,5-dimethyl- t-butylhydrazine sodium toluene                               benzoyl chloride hydrochloride hydroxide and water                            391 2,4-dichlorobenzoyl t-butylhydrazine sodium toluene                         chloride hydrochloride hydroxide and water                                    394 2,3-dimethyl- t-butylhydrazine sodium toluene                               benzoyl chloride hydrochloride hydroxide and water                            449 3,4-dimethyl- t-butylhydrazine sodium toluene                               benzoyl chloride hydrochloride hydroxide and water                            613 2-acetoxybenzoyl t-butylhydrazine NaHCO.sub.3 toluene                       chloride hydrochloride i.e. and water                                           sodium                                                                         bicarbonate                                                                  632 2-methyl-3-chloro- t-butylhydrazine sodium toluene                          benzoyl chloride hydrochloride hydroxide and water                            924 4-chlorobenzoyl methylhydrazine sodium toluene                              chloride   hydroxide                                                          925 3,5-dichlorobenzoyl methylhydrazine sodium toluene                          chloride   hydroxide                                                          926 n-pentanoylchloride t-butylhydrazine sodium toluene                          hydrochloride hydroxide and water                                            927 n-heptanoyl t-butylhydrazine sodium toluene                                 chloride hydrochloride hydroxide and water                                    928 chloroacetyl t-butylhydrazine sodium toluene                                chloride hydrochloride hydroxide and water                                    937 ,-dimethyl t-butylhydrazine sodium toluene                                  acryloyl chloride hydrochloride hydroxide and water                           938 2,3,3-trichloro- t-butylhydrazine sodium toluene                            acryloyl chloride hydrochloride hydroxide and water                           939 cinnamoyl t-butylhydrazine sodium toluene                                   chloride hydrochloride hydroxide and water                                    943 cyclohexanecarbonyl t-butylhydrazine sodium toluene                         chloride hydrochloride hydroxide and water                                    949 2-furoylchloride t-butylhydrazine sodium toluene                             hydrochloride hydroxide and water                                            950 2-thiophene t-butylhydrazine sodium toluene                                 carboxylic acid hydrochloride hydroxide and water                              chloride                                                                      951 pyrrolidine t-butylhydrazine sodium toluene                                 carbonylchloride hydrochloride hydroxide and water                            954 N,N-diethylcarbamoyl t-butylhydrazine sodium toluene                        chloride hydrochloride hydroxide and water                                    959 benzoylchloride 2-tolylhydrazine sodium toluene                               hydroxide and water                                                         961 benzoylchloride phenylhydrazine sodium toluene                                hydroxide and water                                                         963 benzoylchloride 2-chlorophenyl sodium toluene                                hydrazine hydroxide and water                                                964 benzoylchloride 4-chlorophenyl sodium toluene                                hydrazine hydroxide and water                                                965 benzoylchloride benzylhydrazine sodium toluene                                hydroxide and water                                                         967 3,5-dichlorobenzoyl benzylhydrazine sodium toluene                          chloride  hydroxide and water                                                 968 benzoylchloride 4-chloropyrazinyl sodium toluene                             hydrazine hydroxide and water                                                990 n-butanoyl t-butylhydrazine sodium toluene                                  chloride hydrochloride hydroxide and water                                    996 benzoyl N'-(1,1-dimethyl) sodium toluene                                    chloride benzyl-N-benzoyl hydroxide and water                                   hydrazine                                                                  ______________________________________                                    

By following substantially the procedures in Example 16 and using the reactants shown below in Table III, the products of Example Nos. 13, 15, 17, 18, 21 through 31, 33 through 36, 38, 40 through 43, 45, 47 through 54, 56, 57 through 62, 64 through 97, 104 through 109, 113, 117, 118, 119, 121, 122, 123, 125, 126, 130 through 135, 137 through 142, 146, 147, 150, 152 through 154, 160, 163, 167, 173, 175 through 180, 182, 183, 184, 190, 194 through 202, 204 through 211, 214 through 219, 224 through 231, 235 through 249, 251 through 259, 261 through 263, 265 through 270, 272 through 284, 287, 288, 290 through 292, 296, 297, 299 through 307, 309 through 322, 325, 327, 328, 334, 341 through 343, 346 through 348, 355 through 357, 370, 371, 377, 378, 380, 381, 387 through 389, 392, 393, 395, 396, 401 through 413, 419, 420, 422 through 424, 426 through 433, 437 through 448, 450 through 452, 454 through 457, 459 through 469, 474 through 483, 485 through 540, 542 through 545, 548 through 612, 615 through 624, 626 through 631, 633, 929 through 932, 934, 935, 936, 940, 946, 947, 952, 953, 962, 966, 993, 994, 995, 997 and 998 were prepared.

                  TABLE III                                                        ______________________________________                                         Base = Sodium hydroxide except for examples 243 and 408 which                    had no added base, examples 346, 347, 348, 462, and 486 which                  used sodium bicarbonate, and 953 which used no base.                           Solvent = toluene and water except for examples 243 and 408                    which used pyridine, examples 509-515 which used toluene only,                 and example 953 which used methylene chloride only.                            Ex.    Compound of  Compound of Compound of                                    No. Formula III Formula VI Formula IV                                        ______________________________________                                         13   4-toluoyl chloride                                                                          benzoylchloride                                                                              t-butylhydrazine                                   chloride hydrochloride                                                       15 4-toluoyl chloride 4-chlorobenzoyl t-butylhydrazine                           chloride hydrochloride                                                       17 benzoylchloride 3-chlorobenzoyl t-butylhydrazine                              chloride hydrochloride                                                       18 benzoylchloride 2-chlorobenzoyl t-butylhydrazine                              chloride hydrochloride                                                       21 benzoylchloride 4-methylbenzoyl t-butylhydrazine                              chloride hydrochloride                                                       22 benzoylchloride 3-methylbenzoyl t-butylhydrazine                              chloride hydrochloride                                                       23 benzoylchloride 2-methylbenzoyl t-butylhydrazine                              chloride hydrochloride                                                       24 benzoylchloride 4-methoxybenzoyl t-butylhydrazine                             chloride hydrochloride                                                       25 benzoylchloride 3-methoxybenzoyl t-butylhydrazine                             chloride hydrochloride                                                       26 benzoylchloride 2-methoxybenzoyl t-butylhydrazine                             chloride hydrochloride                                                       27 benzoylchloride 4-t-butylbenzoyl t-butylhydrazine                             chloride hydrochloride                                                       28 benzoylchloride 4-cyanobenzoyl t-butylhydrazine                               chloride hydrochloride                                                       29 benzoylchloride 4-nitrobenzoyl t-butylhydrazine                               chloride hydrochloride                                                       30 benzoylchloride 3-nitrobenzoyl t-butylhydrazine                               chloride hydrochloride                                                       31 benzoylchloride 2-nitrobenzoyl t-butylhydrazine                               chloride hydrochloride                                                       33 4-methylbenzoyl 3,4-dichlorobenzoyl t-butylhydrazine                         chloride chloride hydrochloride                                               34 benzoylchloride 4-fluorobenzoyl t-butylhydrazine                              chloride hydrochloride                                                       35 benzoylchloride 3-fluorobenzoyl t-butylhydrazine                              chloride hydrochloride                                                       36 benzoylchloride 2-fluorobenzoyl t-butylhydrazine                              chloride hydrochloride                                                       38 benzoylchloride 2,4-dichlorobenzoyl t-butylhydrazine                          chloride hydrochloride                                                       40 benzoylchloride 4-trifluoromethyl t-butylhydrazine                            benzoylchloride hydrochloride                                                41 benzoylchloride 3-trifluoromethyl t-butylhydrazine                            benzoylchloride hydrochloride                                                42 benzoylchloride 2-trifluoromethyl t-butylhydrazine                            benzoylchloride hydrochloride                                                43 benzoylchloride 2,5-difluorobenzoyl t-butylhydrazine                          chloride hydrochloride                                                       45 benzoylchloride 3-cyanobenzoyl t-butylhydrazine                               chloride hydrochloride                                                       47 benzoylchloride 2,6-difluorobenzoyl t-butylhydrazine                          chloride hydrochloride                                                       48 4-chlorobenzoyl benzoylchloride t-butylhydrazine                             chloride  hydrochloride                                                       49 benzoylchloride 3,4-dichlorobenzoyl t-butylhydrazine                          chloride hydrochloride                                                       50 benzoylchloride 3,5-dichlorobenzoyl t-butylhydrazine                          chloride hydrochloride                                                       51 benzoylchloride 2,6-dichlorobenzoyl t-butylhydrazine                          chloride hydrochloride                                                       52 4-t-butylbenzoyl benzoylchloride t-butylhydrazine                            chloride  hydrochloride                                                       53 2-chlorobenzoyl benzoylchloride t-butylhydrazine                             chloride  hydrochloride                                                       54 1-naphthoylchloride benzoylchloride t-butylhydrazine                           hydrochloride                                                               56 3-chlorobenzoyl benzoylchloride t-butylhydrazine                             chloride  hydrochloride                                                       57 4-chlorobenzoyl 3,4-dichlorobenzoyl t-butylhydrazine                         chloride chloride hydrochloride                                               58 2-chlorobenzoyl 3,4-dichlorobenzoyl t-butylhydrazine                         chloride chloride hydrochloride                                               59 2-methylbenzoyl benzoylchloride t-butylhydrazine                             chloride  hydrochloride                                                       60 benzoylchloride 2-chloro-4-nitro t-butylhydrazine                             benzoylchloride hydrochloride                                                61 benzoylchloride 3,5-dinitrobenzoyl t-butylhydrazine                           chloride hydrochloride                                                       62 benzoylchloride 2,3-dichlorobenzoyl t-butylhydrazine                          chloride hydrochloride                                                       64 benzoylchloride 2-chloro-5-methyl t-butylhydrazine                            benzoylchloride hydrochloride                                                65 benzoylchloride 3,5-dimethylbenzoyl t-butylhydrazine                          chloride hydrochloride                                                       66 benzoylchloride 2-nitro-5-methyl t-butylhydrazine                             benzoylchloride hydrochloride                                                67 benzoylchloride 2-methyl-3-chloro t-butylhydrazine                            benzoylchloride hydrochloride                                                68 benzoylchloride 3-chloro-4-methyl t-butylhydrazine                            benzoylchloride hydrochloride                                                69 benzoylchloride 2-nitro-3-chloro t-butylhydrazine                             benzoylchloride hydrochloride                                                70 benzoylchloride 3-methoxy-4-nitro t-butylhydrazine                            benzoylchloride hydrochloride                                                71 benzoylchloride 2-nitro-3-methoxy t-butylhydrazine                            benzoylchloride hydrochloride                                                72 benzoylchloride 2,4-dinitrobenzoyl t-butylhydrazine                           chloride hydrochloride                                                       73 4-chlorobenzoyl 2-chlorobenzoyl t-butylhydrazine                             chloride chloride hydrochloride                                               74 4-chlorobenzoyl 3-chlorobenzoyl t-butylhydrazine                             chloride chloride hydrochloride                                               75 4-chlorobenzoyl 4-methylbenzoyl t-butylhydrazine                             chloride chloride hydrochloride                                               76 4-chlorobenzoyl 3,5-dichlorobenzoyl t-butylhydrazine                         chloride chloride hydrochloride                                               77 4-chlorobenzoyl 2,4-dichlorobenzoyl t-butylhydrazine                         chloride chloride hydrochloride                                               78 4-chlorobenzoyl 4-trifluoromethyl t-butylhydrazine                           chloride benzoylchloride hydrochloride                                        79 benzoylchloride 4-methanesulfonyl t-butylhydrazine                            benzoylchloride hydrochloride                                                80 benzoylchloride 4-isopropylbenzoyl t-butylhydrazine                           chloride hydrochloride                                                       81 benzoylchloride 2-acetoxybenzoyl t-butylhydrazine                             chloride hydrochloride                                                       82 benzoylchloride 4-ethylbenzoyl t-butylhydrazine                               chloride hydrochloride                                                       83 benzoylchloride 2-bromobenzoyl t-butylhydrazine                               chloride hydrochloride                                                       84 benzoylchloride 4-hydroxybenzoyl t-butylhydrazine                             chloride hydrochloride                                                       85 4-methylbenzoyl 2-methylbenzoyl t-butylhydrazine                             chloride chloride hydrochloride                                               86 4-methylbenzoyl 3-methylbenzoyl t-butylhydrazine                             chloride chloride hydrochloride                                               87 4-methylbenzoyl 2,4-dichlorobenzoyl t-butylhydrazine                         chloride chloride hydrochloride                                               88 4-methylbenzoyl 3,5-dichlorobenzoyl t-butylhydrazine                         chloride chloride hydrochloride                                               89 4-methylbenzoyl 2-chlorobenzoyl t-butylhydrazine                             chloride chloride hydrochloride                                               90 4-methylbenzoyl 4-flourobenzoyl t-butylhydrazine                             chloride chloride hydrochloride                                               91 4-methylbenzoyl 4-trifluoromethyl t-butylhydrazine                           chloride chloride hydrochloride                                               92 4-methylbenzoyl 3-chlorobenzoyl t-butylhydrazine                             chloride chloride hydrochloride                                               93 4-chlorobenzoyl 3-chloromethyl t-butylhydrazine                              chloride chloride hydrochloride                                               94 4-chlorobenzoyl 4-chloromethyl t-butylhydrazine                              chloride chloride hydrochloride                                               95 4-chlorobenzoyl 2-methylbenzoyl t-butylhydrazine                             chloride chloride hydrochloride                                               96 4-chlorobenzoyl 3-methoxybenzoyl t-butylhydrazine                            chloride chloride hydrochloride                                               97 4-chlorobenzoyl 3-methylbenzoyl t-butylhydrazine                             chloride chloride hydrochloride                                               104 benzoylchloride 4-bromobenzoyl t-butylhydrazine                             chloride hydrochloride hydroxide                                              105 benzoylchloride 3-bromobenzoyl t-butylhydrazine                              chloride hydrochloride                                                       106 benzoylchloride 4-n-butylbenzoyl t-butylhydrazine                            chloride hydrochloride                                                       107 4-ethylbenzoyl benzoylchloride t-butylhydrazine                             chloride  hydrochloride                                                       108 3,4-dichloro- benzoylchloride t-butylhydrazine                              benzoylchloride  hydrochloride                                                109 benzoylchloride 4-acetylbenzoyl t-butylhydrazine                             chloride hydrochloride                                                       113 benzoylchloride 2-iodobenzoyl t-butylhydrazine                               chloride hydrochloride                                                       117 benzoylchloride 4-phenoxybenzoyl t-butylhydrazine                            chloride hydrochloride                                                       118 4-trifluoromethyl- benzoylchloride t-butylhydrazine                         benzoylchloride  hydrochloride                                                119 4-trifluoromethyl- 3,4-dichlorobenozyl- t-butylhydrazine                    benzoylchloride chloride hydrochloride                                        121 benzoylchloride 2-chloro-4-bromo- t-butylhydrazine                           benzoylchloride hydrochloride                                                122 benzoylchloride 4-phenylbenzoyl t-butylhydrazine                             chloride hydrochloride                                                       123 benzoylchloride 3,4,5-trimethoxy- t-butylhydrazine                           benzoylchloride hydrochloride                                                125 benzoylchloride 3-thiocyanomethyl- t-butylhydrazine                          benzoylchloride hydrochloride                                                126 benzoylchloride 3-cyanomethyl- t-butylhydrazine                              benzoylchloride hydrochloride                                                130 4-ethylbenzoyl 3-toluoylchloride t-butylhydrazine                           chloride  hydrochloride                                                       131 4-ethylbenzoyl 4-chlorobenzoyl t-butylhydrazine                             chloride chloride hydrochloride                                               132 4-ethylbenzoyl 2-nitrobenzoyl t-butylhydrazine                              chloride chloride hydrochloride                                               133 benzoylchloride 3-ethylbenzoyl t-butylhydrazine                             chloride chloride hydrochloride                                               134 4-ethylbenzoyl 3-bromobenzoyl t-butylhydrazine                              chloride chloride hydrochloride                                               135 4-ethylbenzoyl 2-iodobenzoyl t-butylhydrazine                               chloride chloride hydrochloride                                               137 benzoylchloride 4-carbomethoxy t-butylhydrazine                              benzoylchloride hydrochloride                                                138 2-bromobenzoyl benzoylchloride t-butylhydrazine                             chloride  hydrochloride                                                       139 2-trifluoromethyl- benzoylchloride t-butylhydrazine                         benzoylchloride  hydrochloride                                                140 benzoylchloride 3-iodobenzoyl t-butylhydrazine                               chloride hydrochloride                                                       141 benzoylchloride 2-ethylbenzoyl t-butylhydrazine                              chloride hydrochloride                                                       142 benzoylchloride 3-methoxymethyl t-butylhydrazine                             benzoylchloride hydrochloride                                                146 benzoylchloride 2-nitro-4-(2-chloro t-butylhydrazine                      4-trifluoro- hydrochloride                                                        methyl phenoxy)                                                                benzoylchloride                                                              147 2-nitro-4-(2-chloro benzoylchloride t-butylhydrazine                      4-trifluoromethyl hydrochloride hydrochloride                                    phenoxy) benzoyl                                                               chloride                                                                      150 benzoylchloride 4-methylthio- t-butylhydrazine                               benzoylchloride hydrochloride                                                152 benzoylchloride 3-bromo-4-methyl t-butylhydrazine                            benzoylchloride hydrochloride                                                153 benzoylchloride 3-methyl-4-bromo t-butylhydrazine                            benzoylchloride hydrochloride                                                154 benzoylchloride 2,4-dibromo t-butylhydrazine                                 benzoylchloride hydrochloride                                                160 benzoylchloride 3-phenoxy t-butylhydrazine                                   benzoylchloride hydrochloride                                                163 benzoylchloride 4-formyl benzoyl t-butylhydrazine                            chloride hydrochloride                                                       167 benzoylchloride 2-acetoxybenzoyl t-butylhydrazine                            chloride hydrochloride                                                       173 2-methyl-5-tri- 2-toluoyl chloride t-butylhydrazine                         fluoromethyl  hydrochloride                                                    benzoylchloride                                                               175 4-ethylbenzoyl 3-ethyl t-butylhydrazine                                     chloride benzoylchloride hydrochloride                                        176 benzoylchloride 4-n-propyl t-butylhydrazine                                  benzoylchloride hydrochloride                                                177 4-toluoyl chloride 3-bromo t-butylhydrazine                                  benzoylchloride hydrochloride                                                178 4-toluoyl chloride 3,5-dimethyl t-butylhydrazine                             benzoylchloride hydrochloride                                                179 benzoylchloride 4-iodobenzoyl t-butylhydrazine                               chloride hydrochloride                                                       180 4-toluoyl chloride 4-ethyl benzoyl t-butylhydrazine                          chloride hydrochloride                                                       182 4-toluoyl chloride 3-ethyl benzoyl t-butylhydrazine                          chloride hydrochloride                                                       183 benzoylchloride 2-isopropylbenzoyl t-butylhydrazine                          chloride hydrochloride                                                       184 3-ethyl benzoyl benzoylchloride t-butylhydrazine                            chloride  hydrochloride                                                       190 3-ethyl benzoyl 2,4-dichloro t-butylhydrazine                               chloride benzoylchloride hydrochloride                                        194 4-methoxybenzoyl 3-toluoyl chloride t-butylhydrazine                        chloride  hydrochloride                                                       195 4-methoxybenzoyl benzoylchloride t-butylhydrazine                           chloride  hydrochloride                                                       196 2-chlorobenzoyl 3-toluoyl chloride t-butylhydrazine                         chloride  hydrochloride                                                       197 2-chlorobenzoyl 2-nitrobenzoyl t-butylhydrazine                             chloride chloride hydrochloride                                               198 2-chlorobenzoyl 4-toluoyl chloride t-butylhydrazine                         chloride  hydrochloride                                                       199 2-chlorobenzoyl 4-ethyl benzoyl t-butylhydrazine                            chloride chloride hydrochloride                                               200 4-ethyl benzoyl 3,5-dimethyl t-butylhydrazine                               chloride benzoylchloride hydrochloride                                        201 4-ethyl benzoyl 2-chloro-4-methyl t-butylhydrazine                          chloride benzoylchloride hydrochloride                                         benzoylchloride 3-acetoxybenzoyl t-butylhydrazine                               chloride hydrochloride                                                       204 4-ethyl benzoyl 2-nitro-3-methyl t-butylhydrazine                           chloride benzoylchloride hydrochloride                                        205 4-methoxybenzoyl 3,5-dimethyl t-butylhydrazine                              chloride benzoylchloride hydrochloride                                        206 4-methoxybenzoyl 2,4-dichloro t-butylhydrazine                              chloride benzoylchloride hydrochloride                                        207 2-chlorobenzoyl 2,6-dichloro t-butylhydrazine                               chloride benzoylchloride hydrochloride                                        208 2-chlorobenzoyl 2-bromobenzoyl t-butylhydrazine                             chloride benzoylchloride hydrochloride                                        209 2-chlorobenzoyl 2,5-difluoro t-butylhydrazine                               chloride benzoylchloride hydrochloride                                        210 2-chlorobenzoyl 4-methoxy t-butylhydrazine                                  chloride benzoylchloride hydrochloride                                        211 2-chlorobenzoyl 2-toluoyl chloride t-butylhydrazine                         chloride  hydrochloride                                                       214 2-chlorobenzoyl 2,4-dichlorobenzoyl t-butylhydrazine                        chloride chloride hydrochloride                                               215 2-chlorobenzoyl 3-methoxy t-butylhydrazine                                  chloride benzoylchloride hydrochloride                                        216 2-chlorobenzoyl 3-chlorobenzoyl t-butylhydrazine                            chloride chloride hydrochloride                                               217 2-chlorobenzoyl 2-trifluoromethyl t-butylhydrazine                          chloride benzoylchloride hydrochloride                                        218 2-chlorobenzoyl 3-trifluoromethyl t-butylhydrazine                          chloride benzoylchloride hydrochloride                                        219 2-chlorobenzoyl 4-trifluoromethyl t-butylhydrazine                          chloride benzoylchloride hydrochloride                                        224 2-chlorobenzoyl 4-cyanobenzoyl t-butylhydrazine                             chloride benzoylchloride hydrochloride                                        225 2-chlorobenzoyl 4-fluorobenzoyl t-butylhydrazine                            chloride benzoylchloride hydrochloride                                        226 2-chlorobenzoyl 4-bromobenzoyl t-butylhydrazine                             chloride benzoylchloride hydrochloride                                        227 2-chlorobenzoyl 4-chloro t-butylhydrazine                                   chloride benzoylchloride hydrochloride                                        228 2-chlorobenzoyl 2-methoxy t-butylhydrazine                                  chloride benzoylchloride hydrochloride                                        229 2-chlorobenzoyl 4-nitro t-butylhydrazine                                    chloride benzoylchloride hydrochloride                                        230 2-chlorobenzoyl 2-fluoro t-butylhydrazine                                   chloride benzoylchloride hydrochloride                                        231 2-chlorobenzoyl 2,6-difluoro t-butylhydrazine                               chloride benzoylchloride hydrochloride                                        235 3-methoxybenzoyl 2,5-difluoro t-butylhydrazine                              chloride benzoylchloride hydrochloride                                        236 3-methoxybenzoyl 4-chlorobenzoyl t-butylhydrazine                           chloride benzoylchloride hydrochloride                                        237 3-methoxybenzoyl 3,4-dichloro t-butylhydrazine                              chloride benzoylchloride hydrochloride                                        238 3-methoxybenzoyl benzoylchloride t-butylhydrazine                           chloride  hydrochloride                                                       239 3-methoxybenzoyl 3-toluoyl chloride t-butylhydrazine                        chloride  hydrochloride                                                       240 3-methoxybenzoyl 3,4-dichloro t-butylhydrazine                              chloride benzoylchloride hydrochloride                                        241 3-methoxybenzoyl 4-chlorobenzoyl t-butylhydrazine                           chloride chloride hydrochloride                                               242 3-methoxybenzoyl 2-nitrobenzoyl t-butylhydrazine                            chloride chloride hydrochloride                                               243 benzoylchloride 4-trifluoromethoxy t-butylhydrazine                          benzoylchloride hydrochloride                                                244 4-trifluoromethoxy benzoylchloride t-butylhydrazine                         benzoylchloride  hydrochloride                                                245 4-trifluoromethoxy 3-toluoyl chloride t-butylhydrazine                      benzoylchloride  hydrochloride                                                246 4-trifluoromethoxy 4-chloro benzoyl t-butylhydrazine                        benzoylchloride chloride hydrochloride                                        247 4-trifluoromethoxy 3,4-dichloro t-butylhydrazine                            benzoylchloride benzoylchloride hydrochloride                                 248 4-trifluoromethoxy 4-chlorobenzoyl t-butylhydrazine                         benzoylchloride chloride hydrochloride                                        249 4-trifluoromethoxy 3-toluoyl chloride t-butylhydrazine                      benzoylchloride  hydrochloride                                                251 4-ethoxybenzoyl 3-toluoyl chloride t-butylhydrazine                         chloride  hydrochloride                                                        4-ethoxybenzoyl 3,5-dimethyl t-butylhydrazine                                  chloride benzoylchloride hydrochloride                                        253 4-ethoxybenzoyl benzoylchloride t-butylhydrazine                            chloride  hydrochloride                                                       254 4-ethoxybenzoyl 2-nitro-4-chloro t-butylhydrazine                           chloride benzoylchloride hydrochloride                                        255 3-chloro-4-methoxy- benzoylchloride t-butylhydrazine                        benzoylchloride  hydrochloride                                                256 4-methylthio benzoylchloride t-butylhydrazine                               benzoylchloride  hydrochloride                                                257 4-n-butyloxy 4-chlorobenzoyl t-butylhydrazine                               benzoylchloride chloride hydrochloride                                        258 2-methylthio- benzoylchloride t-butylhydrazine                              benzoylchloride  hydrochloride                                                259 2-nitro-4-chloro- benzoylchloride t-butylhydrazine                          benzoylchloride  hydrochloride                                                261 2-nitro-4-chloro- 4-t-butylbenzoyl t-butylhydrazine                         benzoylchloride  hydrochloride                                                -- 2-nitro-4-chloro- 4-chlorobenzoyl t-butylhydrazine                           benzoylchloride chloride hydrochloride                                        263 4-toluoyl chloride 2-chloro-5-methyl t-butylhydrazine                        benzoylchloride hydrochloride                                                265 4-phenoxybenzoyl benzoylchloride t-butylhydrazine                           chloride  hydrochloride                                                       266 4-phenoxybenzoyl 4-toluoyl chloride t-butylhydrazine                        chloride  hydrochloride                                                       267 4-n-butylbenzoyl benzoylchloride t-butylhydrazine                           chloride  hydrochloride                                                       268 4-n-butylbenzoyl 4-chlorobenzoyl t-butylhydrazine                           chloride chloride hydrochloride                                               269 4-isopropylbenzoyl benzoylchloride t-butylhydrazine                         chloride  hydrochloride                                                       270 4-isopropylbenzoyl 3-toluoyl chloride t-butylhydrazine                      chloride  hydrochloride                                                       271 4-cyanobenzoyl benzoylchloride t-butylhydrazine                             chloride  hydrochloride                                                       273 4-cyanobenzoyl 3-toluoyl chloride t-butylhydrazine                          chloride  hydrochloride                                                       274 2-methyl-4-chloro- benzoylchloride t-butylhydrazine                         benzoylchloride  hydrochloride                                                275 4-ethylbenzoyl 4-trifluoromethoxy t-butylhydrazine                          chloride benzoylchloride hydrochloride                                        276 benzoylchloride 2,3,4,5,6-penta- t-butylhydrazine                            fluoro benzoyl hydrochloride                                                   chloride                                                                     277 2,3,4,5,6-penta- benzoylchloride t-butylhydrazine                            fluoro benzoyl hydrochloride                                                   chloride                                                                     278 4-cyanobenzoyl 3,4-dichlorobenzoyl t-butylhydrazine                         chloride  hydrochloride                                                       279 2-methyl-4-chloro- 3-toluoyl chloride t-butylhydrazine                      benzoylchloride  hydrochloride                                                280 4-trifluoromethyl 3,5-dimethylbenzoyl t-butylhydrazine                      benzoylchloride chloride hydrochloride                                        281 2-methyl-4-chloro- 3,5-dimethylbenzoyl t-butylhydrazine                     benzoylchloride chloride hydrochloride                                        282 benzoylchloride 3-vinylbenzoyl t-butylhydrazine                              chloride hydrochloride                                                       283 4-ethylbenzoyl 3-vinylbenzoyl t-butylhydrazine                              chloride chloride hydrochloride                                               284 4-trifluoromethyl- 3-vinylbenzoyl t-butylhydrazine                          benzoylchloride chloride hydrochloride                                        287 4-n-propylbenzoyl 3,4-dichloro- t-butylhydrazine                            chloride benzoylchloride hydrochloride                                        288 4-n-propylbenzoyl 3-toluoyl chloride t-butylhydrazine                       chloride  hydrochloride                                                       290 4-vinylbenzoyl 3-toluoyl chloride t-butylhydrazine                          chloride  hydrochloride                                                       291 2,6-difluoro- 3,4-dichloro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 292 2,6-difluoro- 3-toluoyl chloride t-butylhydrazine                           benzoylchloride  hydrochloride                                                296 4-chlorobenzoyl 2-bromobenzoyl t-butylhydrazine                             chloride chloride hydrochloride                                               297 4-toluoyl chloride 3-toluoyl chloride 2,2-dimethyl-                          propylhydrazine propylhydrazine                                                oxalic acid salt oxalic acid salt                                            299 4-chlorobenzoyl 3,5-dimethyl- t-butylhydrazine                              chloride benzoylchloride hydrochloride                                        300 3-methoxybenzoyl 3,5-dimethylbenzoyl t-butylhydrazine                       chloride chloride hydrochloride                                               301 4-chlorobenzoyl 4-fluorobenzoyl t-butylhydrazine                            chloride chloride hydrochloride                                               302 4-n-propylbenzoyl 3,5-dimethylbenzoyl t-butylhydrazine                      chloride chloride hydrochloride                                               303 4-vinylbenzoyl 3,5-dimethylbenzoyl t-butylhydrazine                         chloride chloride hydrochloride                                               304 4-acetoxybenzoyl 3,5-dimethylbenzoyl t-butylhydrazine                       chloride chloride hydrochloride                                               305 3,5-dimethyl- benzoylchloride t-butylhydrazine                              benzoylchloride  hydrochloride                                                306 3,5-dimethyl- 3-toluoyl chloride t-butylhydrazine                           benzoylchloride  hydrochloride                                                307 3,5-dimethyl- 4-ethylbenzoyl t-butylhydrazine                               benzoylchloride chloride hydrochloride                                        309 4-isopropyl- 3,5-dimethyl t-butylhydrazine                                  benzoylchloride benzoylchloride hydrochloride                                 310 4-ethylbenzoyl 2-bromobenzoyl t-butylhydrazine                              chloride chloride hydrochloride                                               311 3-chloro-4-methyl- benzoylchloride t-butylhydrazine                         benzoylchloride  hydrochloride                                                312 3-chloro-4-methyl- benzoylchloride t-butylhydrazine                         benzoylchloride  hydrochloride                                                313 3-chloro-4-methyl- 3-toluoyl chloride t-butylhydrazine                      benzoylchloride  hydrochloride                                                314 3-chloro-4-methyl- 3,4-dichlorobenzoyl t-butylhydrazine                     benzoylchloride chloride hydrochloride                                        315 4-ethylbenzoyl 2-nitrobenzoyl 2,2-dimethyl-                                 chloride chloride propylhydrazine                                               oxalic acid salt                                                             316 2,6-difluoro- 2-chlorobenzoyl t-butylhydrazine                              benzoylchloride chloride hydrochloride                                        317 2,6-difluoro- 3-chlorobenzoyl t-butylhydrazine                              benzoylchloride chloride hydrochloride                                        318 2,6-difluoro- 4-chlorobenzoyl t-butylhydrazine                              benzoylchloride chloride hydrochloride                                        319 2,6-difluoro- 3,5-dimethylbenzoyl t-butylhydrazine                          benzoylchloride chloride hydrochloride                                        320 4-ethylbenzoyl 3,5-dimethylbenzoyl 2,2-dimethyl-                            chloride chloride propylhydrazine                                                oxalic acid salt                                                            321 3-trifluoromethyl- 4-chlorobenzoyl t-butylhydrazine                         benzoylchloride chloride hydrochloride                                        322 3-trifluoromethyl- 3,5-dimethyl- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 325 2-nitro-3-methoxy- 3-toluoyl chloride t-butylhydrazine                      benzoylchloride  hydrochloride                                                327 4-chlorobenzoyl 4-carboxymethyl- t-butylhydrazine                           chloride benzoylchloride hydrochloride                                        328 4-ethylbenzoyl 4-carboxymethyl- t-butylhydrazine                            chloride benzoylchloride hydrochloride                                        334 4-ethylbenzoyl 3,5-dichloro- t-butylhydrazine                               chloride benzoylchloride hydrochloride                                        341 4-chlorobenzoyl 2-fluorobenzoyl t-butylhydrazine                            chloride chloride hydrochloride                                               342 4-ethylbenzoyl 3,4-dichloro- t-butylhydrazine                               chloride benzoylchloride hydrochloride                                        343 4-ethylbenzoyl 2-fluorobenzoyl t-butylhydrazine                             chloride chloride hydrochloride                                               346 4-carboxymethyl- 4-chlorobenzoyl t-butylhydrazine                           benzoylchloride chloride hydrochloride                                        347 4-carboxymethyl- 3,5-dimethyl- t-butylhydrazine                             benzoylchloride benzoylchloride hydrochloride                                    bonate                                                                      348 4-carboxymethyl- 3-toluoyl chloride t-butylhydrazine                        benzoylchloride  hydrochloride                                                   bonate                                                                      355 3-phenoxybenzoyl benzoylchloride t-butylhydrazine                           chloride  hydrochloride                                                       356 3-phenoxybenzoyl 3-toluoyl chloride t-butylhydrazine                        chloride  hydrochloride                                                       357 4-acetylbenzoyl 3-toluoyl chloride t-butylhydrazine                         chloride  hydrochloride                                                       370 4-biphenylbenzoyl 3-toluoyl chloride t-butylhydrazine                       chloride  hydrochloride                                                       371 3-cyanobenzoyl 3-toluoyl chloride t-butylhydrazine                          chloride  hydrochloride                                                       377 3-chloromethyl- 3-toluoyl chloride t-butylhydrazine                         benzoylchloride  hydrochloride                                                378 4-ethylbenzoyl 2,3-dimethylbenzoyl t-butylhydrazine                         chloride chloride hydrochloride                                               380 benzoylchloride 2,3-dimethylbenzoyl t-butylhydrazine                         chloride hydrochloride                                                       381 4-toluoyl chloride 2,3-dimethylbenzoyl t-butylhydrazine                      chloride hydrochloride                                                       387 benzoylchloride 1-naphthoyl t-butylhydrazine                                 chloride hydrochloride                                                       388 1-naphthoyl 3-toluoyl chloride t-butylhydrazine                             chloride  hydrochloride                                                       389 4-isothiocyanato- 3-toluoyl chloride t-butylhydrazine                       benzoylchloride  hydrochloride                                                392 2-fluorobenzoyl 2-bromobenzoyl t-butylhydrazine                             chloride chloride hydrochlorider                                              393 2-fluorobenzoyl 3-toluoyl chloride t-butylhydrazine                         chloride  hydrochloride                                                       395 2-fluorobenzoyl 2-nitrobenzoyl t-butylhydrazine                             chloride chloride hydrochloride                                               396 2-fluorobenzoyl benzoylchloride t-butylhydrazine                            chloride  hydrochloride                                                       401 4-bromobenzoyl benzoylchloride t-butylhydrazine                             chloride  hydrochloride                                                       402 2,3-dichloro- 2-bromobenzoyl t-butylhydrazine                               benzoylchloride chloride hydrochloride                                        403 2,3-dichloro- benzoylchloride t-butylhydrazine                              benzoylchloride  hydrochloride                                                404 2-fluorobenzoyl 3,5-dimethyl- t-butylhydrazine                              chloride benzoylchloride hydrochloride                                        405 2,3-dichloro- 3-toluoyl chloride t-butylhydrazine                           benzoylchloride  hydrochloride                                                406 benzoylchloride 2-naphthoyl t-butylhydrazine                                 chloride hydrochloride                                                       407 2-naphthoyl 3-toluoyl chloride t-butylhydrazine                             chloride  hydrochloride                                                       408 benzoylchloride 3-trifluoromethoxy- t-butylhydrazine                         benzoylchloride hydrochloride                                                409 4-isothiocyanato- benzoylchloride t-butylhydrazine                          benzoylchloride  hydrochloride                                                410 2,6-difluoro- 2,4-difluoro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 411 2,6-difluoro- 3,5-dichloro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 412 4-toluoyl 3,5-bis-(trifluoro- t-butylhydrazine                              chloride methyl)benzoyl hydrochloride                                         413 benzoylchloride 3,5-bis-(trifluoro- t-butylhydrazine                         methyl)benzoyl hydrochloride                                                   chloride                                                                     419 benzoylchloride 3-chloro-4-fluoro- t-butylhydrazine                          benzoylchloride hydrochloride                                                420 4-chlorobenzoyl 3-chloro-4-fluoro- t-butylhydrazine                         chloride benzoylchloride hydrochloride                                        422 4-chlorobenzoyl 3,5-bis-(trifluoro- t-butylhydrazine                        chloride methyl)benzoyl hydrochloride                                           chloride                                                                     423 2,3-dimethyl- 3,4-dichloro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 424 4-toluoyl chloride 3-chloro-2-methyl- t-butylhydrazine                      benzoylchloride hydrochloride hydroxide                                       426 2,6-dimethyl- 3-toluoyl chloride t-butylhydrazine                           benzoylchloride  hydrochloride                                                427 2,6-dimethyl- 3,5-dimethyl- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 428 2,3-dimethyl- 2-bromobenzoyl t-butylhydrazine                               benzoylchloride chloride hydrochloride                                        429 2,3-dimethyl- 3,5-dimethyl- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 430 2,3-dimethyl- 3-chlorobenzoyl t-butylhydrazine                              benzoylchloride chloride hydrochloride                                        431 3-trifluoro- benzoylchloride t-butylhydrazine                               methoxybenzoyl  hydrochloride                                                  chloride                                                                      432 3-trifluoro- 3-toluoyl chloride t-butylhydrazine                            methoxybenzoyl  hydrochloride                                                  chloride                                                                      433 2,3-dimethyl- 2-methyl-3-chloro- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 437 2,6-difluoro- 2-bromobenzoyl t-butylhydrazine                               benzoylchloride chloride hydrochloride                                        438 2-methyl-3-chloro- 3,5-dimethyl- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 439 2-methyl-3-chloro- 3-chloro-4-fluoro- t-butylhydrazine                      benzoylchloride benzoylchloride hydrochloride                                 440 2,3-dimethyl- 3-chloro-4-fluoro- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 441 4-ethylbenzoyl 3-chloro-4-fluoro- t-butylhydrazine                          chloride benzoylchloride hydrochloride                                        442 3,4-dimethyl benzoylchloride t-butylhydrazine                               benzoylchloride  hydrochloride                                                443 3,4-dimethyl- 3-toluoyl chloride t-butylhydrazine                           benzoylchloride  hydrochloride                                                444 3,4-dimethyl- 2-chlorobenzoyl t-butylhydrazine                              benzoylchloride chloride hydrochloride                                        445 3,4-dimethyl- 2,4-dichloro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 446 3,4-dimethyl- 2-bromobenzoyl t-butylhydrazine                               benzoylchloride chloride hydrochloride                                        447 3,4-dimethyl- 3,5-dimethyl- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 448 3,4-dimethyl- 2-nitrobenzoyl t-butylhydrazine                               benzoylchloride chloride hydrochloride                                        450 benzoylchloride 3,4-dimethyl- t-butylhydrazine                               benzoylchloride hydrochloride                                                451 4-ethylbenzoyl 3,4-dimethyl- t-butylhydrazine                               chloride benzoylchloride hydrochloride                                        452 2-fluoro-6-chloro- 3-toluoyl chloride t-butylhydrazine                      benzoylchloride  hydrochloride                                                454 4-chloromethyl benzoylchloride t-butylhydrazine                             benzoylchloride  hydrochloride                                                455 2,3-dimethoxy- benzoylchloride t-butylhydrazine                             benzoylchloride  hydrochloride                                                456 2,3-dimethoxy- 4-chlorobenzoyl t-butylhydrazine                             benzoylchloride chloride hydrochloride                                        457 2,3-dimethoxy- 2-bromobenzoyl t-butylhydrazine                              benzoylchloride chloride hydrochloride                                        459 4-t-butylbenzoyl 3,4-dimethyl- t-butylhydrazine                             chloride benzoylchloride hydrochloride                                        460 4-t-butylbenzoyl 3,5-dimethyl- t-butylhydrazine                             chloride benzoylchloride hydrochloride                                        461 4-t-butylbenzoyl 2,4-dichloro- t-butylhydrazine                             chloride benzoylchloride hydrochloride                                        462 4-t-butylbenzoyl 2-nitrobenzoyl t-butylhydrazine                            chloride chloride hydrochloride                                               463 4-t-butylbenzoyl 2-bromobenzoyl t-butylhydrazine                            chloride chloride hydrochloride                                               464 4-t-butylbenzoyl 3-toluoyl chloride t-butylhydrazine                        chloride  hydrochloride                                                       465 4-t-butylbenzoyl 2-chlorobenzoyl t-butylhydrazine                           chloride chloride hydrochloride                                               466 4-t-butylbenzoyl 3,4-dichloro- t-butylhydrazine                             chloride benzoylchloride hydrochloride                                        467 3,4-dimethyl- 3,4-dichloro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 468 3,4-dimethyl- 4-fluorobenzoyl t-butylhydrazine                              benzoylchloride chloride hydrochloride                                        469 4-t-butylbenzoyl 4-fluorobenzoyl t-butylhydrazine                           chloride chloride hydrochloride                                               474 1-naphthoyl 2,4-dichloro- t-butylhydrazine                                  chloride benzoylchloride hydrochloride                                        475 1-naphthoyl 2-bromobenzoyl t-butylhydrazine                                 chloride chloride hydrochloride                                               476 2-methyl-3-nitro- benzoylchloride t-butylhydrazine                          benzoylchloride  hydrochloride                                                477 2-methyl-3-nitro- 3-toluoyl chloride t-butylhydrazine                       benzoylchloride  hydrochloride                                                478 2-methyl-3-nitro- 4-chlorobenzoyl t-butylhydrazine                          benzoylchloride chloride hydrochloride                                        479 2-methyl-3-nitro- 2,4-dichloro- t-butylhydrazine                            benzoylchloride benzoylchloride hydrochloride                                 480 3-bromo-2-methyl- benzoylchloride t-butylhydrazine                          benzoylchloride  hydrochloride                                                481 3-bromo-2-methyl- 3-toluoylchloride t-butylhydrazine                        benzoylchloride  hydrochloride                                                482 3-bromo-2-methyl- 4-chlorobenzoyl t-butylhydrazine                          benzoylchloride chloride hydrochloride                                        483 3-bromo-2-methyl- 2,4-dichlorobenzoyl t-butylhydrazine                      benzoylchloride chloride hydrochloride                                        485 2-toluoyl chloride 2-bromobenzoyl t-butylhydrazine                           chloride hydrochloride                                                       486 2-toluoyl chloride 2-nitrobenzoyl t-butylhydrazine                           chloride hydrochloride                                                       487 2-toluoyl chloride 3-nitrobenzoyl t-butylhydrazine                           chloride hydrochloride                                                       488 2-toluoyl chloride 4-chlorobenzoyl t-butylhydrazine                          chloride hydrochloride                                                       489 2-toluoyl chloride 3-toluoyl chloride t-butylhydrazine                        hydrochloride                                                               490 2-toluoyl chloride 3,5-dimethyl- t-butylhydrazine                            benzoylchloride hydrochloride                                                491 2-toluoyl chloride 3,4-dichloro- t-butylhydrazine                            benzoylchloride hydrochloride                                                492 2-toluoyl chloride 3,5-dichloro- t-butylhydrazine                            benzoylchloride hydrochloride                                                493 2-methyl-3-fluoro- benzoylchloride t-butylhydrazine                         chloride  hydrochloride                                                       494 2-methyl-3-fluoro- 3-toluoyl chloride t-butylhydrazine                      benzoylchloride  hydrochloride                                                495 2-fluoro-6-chloro- benzoylchloride t-butylhydrazine                         benzoylchloride  hydrochloride                                                496 2-fluoro-6-chloro- 2,4-dichloro- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 497 2-fluoro-6-chloro- 4-fluorobenzoyl t-butylhydrazine                         benzoylchloride chloride hydrochloride                                        498 4-(2-chloroethyl)- 3,5-dimethyl- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 499 2,4,6-trifluoro- benzoylchloride t-butylhydrazine                           benzoylchloride  hydrochloride                                                500 2,4,6-trifluoro- 2,4-dichloro- t-butylhydrazine                             benzoylchloride benzoylchloride hydrochloride                                 501 2,4,6-trifluoro- 2-bromobenzoyl t-butylhydrazine                            benzoylchloride chloride hydrochloride                                        502 2,4,6-trifluoro- 3,5-dimethyl t-butylhydrazine                              benzoylchloride benzoylchloride hydrochloride                                 503 2-nitro-3-chloro- benzoylchloride t-butylhydrazine                          benzoylchloride  hydrochloride                                                503 2-nitro-3-chloro- 2-bromobenzoyl t-butylhydrazine                           benzoylchloride chloride hydrochloride                                        504 2-nitro-3-chloro- 2-nitrobenzoyl t-butylhydrazine                           benzoylchloride chloride hydrochloride                                        505 2-nitro-3-chloro- 3-toluoyl t-butylhydrazine                                benzoylchloride chloride hydrochloride                                        506 2-nitro-3-chloro- 3-chlorobenzoyl t-butylhydrazine                          benzoylchloride chloride hydrochloride                                        507 2-nitro-3-chloro- 2,4-dichloro- t-butylhydrazine                            benzoylchloride benzoylchloride hydrochloride                                 508 2-nitro-3-chloro- 3,5-dichloro- t-butylhydrazine                            benzoylchloride benzoylchloride hydrochloride                                 509 2-nitro-3-chloro- 3,5-dimethyl- t-butylhydrazine                            benzoylchloride benzoylchloride hydrochloride                                 510 4-ethylbenzoyl 2,3-difluoro- t-butylhydrazine                               chloride benzoylchloride hydrochloride                                        511 4-ethylbenzoyl 2,3-dichloro- t-butylhydrazine                               chloride benzoylchloride hydrochloride                                        512 2,3-difluoro- benzoylchloride t-butylhydrazine                              benzoylchloride  hydrochloride                                                513 2,3-dichloro- 2-nitrobenzoyl t-butylhydrazine                               benzoylchloride chloride hydrochloride                                        514 benzoylchloride 2,3-difluoro- t-butylhydrazine                               benzoylchloride hydrochloride                                                516 2,3-dichloro- 3,5-dimethyl- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 517 2,3-dichloro- 2,4-dichloro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 518 2,3-dichloro- 3,5-dichloro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 519 2,3-dichloro- 3-chlorobenzoyl t-butylhydrazine                              benzoylchloride chloride hydrochloride                                        520 2,3-dichloro- 2,3-dimethyl- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 521 2,3-difluoro- 2-bromobenzoyl t-butylhydrazine                               benzoylchloride chloride hydrochloride                                        522 2,3-dimethyl- 4-chlorobenzoyl t-butylhydrazine                              benzoylchloride chloride hydrochloride                                        523 2,3-dimethyl- 2,4-dichloro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 524 2,3-dimethyl- 2,6-difluoro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 525 2,3-dimethyl- 2,4-difluoro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 526 2,3-dimethyl- 3-methoxybenzoyl t-butylhydrazine                             benzoylchloride chloride hydrochloride                                        527 2,3-dimethyl- 2-methoxybenzoyl t-butylhydrazine                             benzoylchloride chloride hydrochloride                                        528 2,3-dimethyl- 2-toluoyl chloride t-butylhydrazine                           benzoylchloride  hydrochloride                                                529 2,3-dimethyl- 4-toluoyl chloride t-butylhydrazine                           benzoylchloride  hydrochloride                                                530 2-methyl-3-chloro- 2,4-dichlorobenzoyl t-butylhydrazine                     benzoylchloride chloride hydrochloride                                        531 4-(2-chloro- benzoylchloride t-butylhydrazine                               ethyl)benzoyl  hydrochloride                                                   chloride                                                                      532 4-(2-chloro- 2,4-dichloro- t-butylhydrazine                                 ethyl)benzoyl benzoylchloride hydrochloride                                    chloride                                                                      533 3-fluoro-4-methyl- 3,5-dimethyl- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 534 3-fluoro-4-methyl- 3,5-difluoro- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 535 3-fluoro-4-methyl- 3-toluoyl chloride t-butylhydrazine                      benzoylchloride  hydrochloride                                                536 3-fluoro-4-methyl- 3,5-dichloro- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 537 3-fluoro-4-methyl- 2-nitrobenzoyl t-butylhydrazine                          benzoylchloride chloride hydrochloride                                        538 3-fluoro-4-methyl- 2,4-dichloro- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 539 4-ethylbenzoyl 3,5-difluoro- t-butylhydrazine                               chloride benzoylchloride hydrochloride                                        540 2,3-dimethyl- 2-iodobenzoyl t-butylhydrazine                                benzoylchloride chloride hydrochloride                                        542 2,6-difluoro-3- benzoylchloride t-butylhydrazine                            methylbenzoyl  hydrochloride                                                   chloride                                                                      543 2,6-difluoro-3- 3-toluoyl chloride t-butylhydrazine                         methylbenzoyl  hydrochloride                                                   chloride                                                                      544 2,6-difluoro-3- 2,4-dichloro- t-butylhydrazine                              methylbenzoyl  hydrochloride                                                   chloride                                                                      545 4-chlorobenzoyl 2,3-dimethyl- t-butylhydrazine                              chloride benzoylchloride hydrochloride                                        548 2-fluoro-6-chloro- 2,3-difluorobenzoyl t-butylhydrazine                     benzoylchloride chloride hydrochloride                                        549 2,3-difluoro- 2-nitrobenzoyl t-butylhydrazine                               benzoylchloride chloride hydrochloride                                        550 2,3-difluoro- 3-toluoyl chloride t-butylhydrazine                           benzoylchloride  hydrochloride                                                551 2,3-difluoro- 3,5-dimethyl- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 552 2,3-difluoro- 2,4-dichloro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 553 2,3-dimethyl- 2,3-difluoro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 554 2,3-dimethyl- 2,3-dichloro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 555 2,3-dimethyl- 3,4-dimethyl- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 556 2,3-dimethyl- 2-nitrobenzoyl t-butylhydrazine                               benzoylchloride chloride hydrochloride                                        557 4-ethylbenzoyl 2-methyl-5-chloro- t-butylhydrazine                          chloride benzoylchloride hydrochloride                                        558 2,3-dimethyl- benzoylchloride t-butylhydrazine                              benzoylchloride  hydrochloride                                                559 benzoylchloride 2-methyl-5-chloro- t-butylhydrazine                         benzoylchloride hydrochloride hydroxide                                       560 2,6-difluoro- 2-methyl-5-chloro- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 561 2,3-dimethyl- 2-methyl-5-chloro- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 562 2-methyl-3-chloro- 2-methyl-5-chloro- t-butylhydrazine                      benzoylchloride benzoylchloride hydrochloride                                 563 2,6-difluoro- 2-chloro-5-methyl- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 564 2,3-dimethyl- 2-chloro-5-methyl- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 565 2-methyl-3-chloro- 2-chloro-5-methyl- t-butylhydrazine                      benzoylchloride benzoylchloride hydrochloride                                 566 4-chlorobenzoyl 2-methyl-5-chloro- t-butylhydrazine                         chloride benzoylchloride hydrochloride                                        567 4-chlorobenzoyl 2-chloro-5-methyl- t-butylhydrazine                         chloride benzoylchloride hydrochloride                                        568 2-flouro-4-chloro- benzoylchloride t-butylhydrazine                         benzoylchloride  hydrochloride                                                569 2-flouro-4-chloro- 3-tolyl chloride t-butylhydrazine                        benzoylchloride  hydrochloride                                                570 2-flouro-4-chloro- 3,5-dimethyl t-butylhydrazine                            benzoylchloride benzoylchloride hydrochloride                                 571 2-flouro-4-chloro- 3,5-dichloro- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 572 2-flouro-4-chloro- 2-bromobenzoyl t-butylhydrazine                          benzoylchloride chloride hydrochloride                                        573 2-flouro-4-chloro- 2-nitrobenzoyl t-butylhydrazine                          benzoylchloride chloride hydrochloride                                        574 2-chloro-3-methyl- 2,4-dichloro- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 575 2-chloro-3-methyl- benzoylchloride t-butylhydrazine                         benzoylchloride                                                               576 2-chloro-3-methyl- 3-toluoyl chloride t-butylhydrazine                      benzoylchloride  hydrochloride                                                577 2-chloro-3-methyl- 3,5-dimethyl- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 578 2-chloro-3-methyl- 3,5-dichloro- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 579 2-bromo-3-methyl- 3,5-dimethyl- t-butylhydrazine                            benzoylchloride benzoylchloride hydrochloride                                 580 2-bromo-3-methyl- 2,4-dichloro- t-butylhydrazine                            benzoylchloride benzoylchloride hydrochloride                                 581 2-bromo-3-methyl- 3-toluoyl chloride t-butylhydrazine                       benzoylchloride  hydrochloride                                                582 2-bromo-3-methyl- 3,5-dichloro- t-butylhydrazine                            benzoylchloride benzoylchloride hydrochloride                                 583 2-bromo-3-methyl- 2-bromobenzoyl t-butylhydrazine                           benzoylchloride chloride hydrochloride                                        584 2,3-dimethyl- 2-chlorobenzoyl t-butylhydrazine                              benzoylchloride chloride hydrochloride                                        585 2,3-dimethyl- 2-trifluoromethyl- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 586 2,3-dimethyl- 4-ethylbenzoyl t-butylhydrazine                               benzoylchloride chloride hydrochloride                                        587 2,3-dimethyl- 3,5-dichloro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 588 2,6-difluoro- 3-chloro-4-fluoro- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 589 4-chlorobenzoyl 3,5-difluoro- t-butylhydrazine                              chloride benzoylchloride hydrochloride                                        590 2,3-dimethyl- 3,5-difluoro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 591 2-methyl-3-chloro- 3,5-difluoro- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 592 benzoylchloride 3,5-difluoro- t-butylhydrazine                               benzoylchloride hydrochloride                                                593 4-ethylbenzoyl 2,5-dimethyl- t-butylhydrazine                               chloride benzoylchloride hydrochloride                                        594 2,6-difluoro- 3,5-difluoro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 595 2-methyl-3-chloro- 3,5-dichloro- t-butylhydrazine                           benzoylchloride benzoylchloride hydrochloride                                 596 2,3-dimethyl- 2,5-dimethyl- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 597 2-bromobenzoyl 3,5-dimethyl- t-butylhydrazine                               chloride benzoylchloride hydrochloride                                        598 2-bromo-3-methyl- 3-chlorobenzoyl t-butylhydrazine                          benzoylchloride chloride hydrochloride                                        599 2-chloro-3-methyl- 3-chlorobenzoyl t-butylhydrazine                         benzoylchloride chloride hydrochloride                                        600 2-chloro-3-methyl- 3-chlorobenzoyl t-butylhydrazine                         benzoylchloride chloride hydrochloride                                        601 2-chloro-3-methyl- 2-nitrobenzoyl t-butylhydrazine                          benzoylchloride chloride hydrochloride                                        602 2,3-dimethyl- 2-nitro-3-methyl- t-butylhydrazine                            benzoylchloride benzoylchloride hydrochloride                                 603 2,3-dimethyl- 2-nitro-5-methyl- t-butylhydrazine                            benzoylchloride benzoylchloride hydrochloride                                 604 2,6-difluoro- benzoylchloride t-butylhydrazine                              benzoylchloride  hydrochloride                                                605 2,6-dimethyl- 2,4-dichloro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 606 2,4,6-trimethyl- 3,5-dimethyl- t-butylhydrazine                             benzoylchloride benzoylchloride hydrochloride                                 607 2,4,6-trimethyl- 2,4-dichloro- t-butylhydrazine                             benzoylchloride benzoylchloride hydrochloride                                 608 2,6-difluoro- 4-toluoyl chloride t-butylhydrazine                           benzoylchloride                                                               609 2,6-difluoro- 2,5-dichloro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 610 2,4,6-trimethyl- 4-chlorobenzoyl t-butylhydrazine                           benzoylchloride chloride hydrochloride                                        611 2,4,6-trimethyl- 3-toluoyl chloride t-butylhydrazine                        benzoylchloride  hydrochloride                                                612 2,4,6-trimethyl- 3,4-dichloro- t-butylhydrazine                             benzoylchloride benzoylchloride hydrochloride                                 615 2,4-dimethyl- 3-toluoyl chloride t-butylhydrazine                           benzoylchloride  hydrochloride                                                616 2,4-dimethyl- 2,4-dichloro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 617 2,4-dimethyl- 3,5-dimethyl- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 618 2,4-dimethyl- 3,5-dichloro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 619 2,4-dimethyl- 3-bromobenzoyl t-butylhydrazine                               benzoylchloride chloride hydrochloride                                        620 2,4-dimethyl- 3,4-dichloro- t-butylhydrazine                                benzoylchloride benzoylchloride hydrochloride                                 621 2-bromo-3-methyl- 2-nitrobenzoyl t-butylhydrazine                           benzoylchloride chloride hydrochloride                                        622 piperonyl chloride benzoylchloride t-butylhydrazine                           hydrochloride                                                               623 piperonyl chloride 4-chlorobenzoyl t-butylhydrazine                          chloride hydrochloride                                                       624 piperonyl chloride 3-toluoyl chloride t-butylhydrazine                        hydrochloride                                                               626 2-pyrrolobenzoyl benzoylchloride t-butylhydrazine                           chloride  hydrochloride                                                       627 2-pyrrolobenzoyl 3-toluoyl chloride t-butylhydrazine                        chloride  hydrochloride                                                       628 2,3-dimethyl- 2-bromo-5-methyl- t-butylhydrazine                            benzoylchloride benzoylchloride hydrochloride                                 629 2-methyl-3-chloro- 3-chlorobenzoyl t-butylhydrazine                         benzoylchloride chloride hydrochloride                                        630 2-methyl-3-chloro- 4-fluorobenzoyl t-butylhydrazine                         benzoylchloride chloride hydrochloride                                        631 2-methyl-3-chloro- 2-bromobenzoyl t-butylhydrazine                          benzoylchloride chloride hydrochloride                                        633 2-methyl-3-chloro- 3,5-dimethyl-4 t-butylhydrazine                          benzoylchloride chlorobenzoyl hydrochloride                                     chloride                                                                     929 n-pentanoyl 2-furoylchloride t-butylhydrazine                               chloride  hydrochloride                                                       930 ethylchloroformate n-pentanoylchloride t-butylhydrazine                       hydrochloride                                                               931 ethylchloroformate 4-chlorobenzoyl t-butylhydrazine                           hydrochloride                                                               932 benzoylchloride ethylchoro t-butylhydrazine                                 formate hydrochloride hydroxide                                               934 phenylchloro- benzoylchloride t-butylhydrazine                              formate  hydrochloride                                                        935 benzoylchloride phenylchloro t-butylhydrazine                                formate hydrochloride                                                        936 benzoylchloride 4-nitrophenyl t-butylhydrazine                               chloroformate hydrochloride                                                  940 4-ethylbenzoyl phenylpropiolyl t-butylhydrazine                             chloride chloride hydrochloride                                               945 4-chlorobenzoyl 4-phenylbenzoyl t-butylhydrazine                            chloride chloride hydrochloride                                               946 benzoylchloride 1,2,3,4-tetrahydro- t-butylhydrazine                         2-naphthoylchloride hydrochloride                                            947 prolinecarboxylic 3-toluoyl chloride t-butylhydrazine                       acid chloride                                                                 952 benzoylchloride N,N-diethylcarbamoyl t-butylhydrazine                        chloride hydrochloride                                                       953 benzoylchloride p-chlorophenyl t-butylhydrazine                              isocyanate hydrochloride                                                     962 3,5-dichlorobenzoyl chloroacetyl phenylhydrazine                            chloride chloride                                                             966 3,5-dichlorobenzoyl chloroacetyl benzylhydrazine                            chloride chloride                                                             993 n-pentanoyl ethylchloro t-butylhydrazine                                     formate hydrochloride                                                        994 4-chlorobenzoyl- ethylchloro t-butylhydrazine                               chloride formate hydrochloride                                                995 2,6-difluoro- ethylchloro t-butylhydrazine                                  benzoylchloride formate hydrochloride                                         997 benzoylchloride 3-chlorobenzoyl N'-(1,1-di-                                  chloride methyl)benzyl-N-                                                       benzoyl                                                                        hydrazine                                                                   998 benzoylchloride 2,3-dichloro- N'-(1,1-di-                                    benzoylchloride methyl)benzyl-N-                                                benzoyl                                                                        hydrazine                                                                 ______________________________________                                    

By following substantially the procedures in Example 44 and using the reactants shown below in Table IV, the products of Example Nos. 39, 46, 63, 110, 111, 112, 114, 115, 116, 120, 124, 127, 128, 129, 136, 143, 155 through 158, 185 through 189, 332, 336 through 340, 382, 383, 384, 399, 400, 414 through 418, 421, 434, 435, 436, 453, 470, 471, 472, 546, 547, 634 and 955 through 960 were prepared.

                  TABLE IV                                                         ______________________________________                                         Ex.                                                                              No.  Reactants                                                               ______________________________________                                          39  Compound of Formula VII:                                                                        Benzoylhydrazine                                            Compound of Formula VIII: Dimethyl ketone                                      Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of acetone                            Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 2-isopropyl-1-benzoylhydrazine                          Compound of Formula VI: Benzoylchloride                                        Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                     46 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VII: Methylethyl ketone                                    Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of 2-butanone                         Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                       butyl-1-benzoylhydrazine  2-sec                                                   Compound of Formula VI: Benzoylchloride                                        Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                     63 Compound of Formula VII: Benzoylhydrazine                                butyl ketone f Formula VIII: Methyl-t                                             Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of methyl-t-                           butylketone                                                                   Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 2-(1,2,2-trimethylpropyl)-1-                             benzoylhydrazine                                                              Compound of Formula VI: Benzoylchloride                                        Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    110 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: 1,1,1-trimethylacetaldehyde                          Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of 1,1,1-                              trimethylacetaldehyde                                                         Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 2-neopentyl-1-benzoylhydrazine                          Compound of Formula VI: 2-bromobenzoylchloride                                 Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    111 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: 1,1,1-trimethylacetaldehyde                          Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of 1,1,1-                              trimethylacetaldehyde                                                         Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X 2-neopentyl-1-benzoylhydrazine                           Compound of Formula VI: 2-nitrobenzoylchloride                                 Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    112 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: 1,1,1-trimethylacetaldehyde                          Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of 1,1,1-                              trimethylacetaldehyde                                                         Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 2-neopentyl-1-benzoylhydrazine                          Compound of Formula VI: 2-anisoyl chloride                                     Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    114 Compound of Formula VII. Benzoylhydrazine                                   Compound of Formula VIII: Isobutyraldehyde                                     Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of isobutyr-                           aldehyde                                                                      Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic Acid                                                          Compound of Formula X: 2-isobutyl-1-benzoylhydrazine                           Compound of Formula VI: Benzoylchloride                                        Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    115 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Acetone                                              Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of acetone                            Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 2-isopropyl-1-benzoylhydrazine                          Compound of Formula VI: 2-bromobenzoylchloride                                 Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    116 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Acetone                                              Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of acetone                            Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X 2-isopropyl-1-benzoylhydrazine                           Compound of Formula VI: 3,4-dichlorobenzoylchloride                            Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    120 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Dicyclopropylketone                                  Solvent: Methanol                                                              Catalyst: Acetic Acid                                                          Compound of Formula IX: Benzoylhydrazone of dicyclo-                            propylketone                                                                  Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 2-dicyclopropylmethyl-1-benzoyl-                         hydrazine                                                                     Compound of Formula VI: Benzoylchloride                                        Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    124 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Methyl-t-butyl ketone                                Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of methyl-t-                           butylketone                                                                   Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 2-(1,2,2-trimethylpropyl)-1-                             benzoylhydrazine                                                              Compound of Formula VI: 2-nitrobenzoylchloride                                 Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    127 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Methyl-t-butyl ketone                                Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of methyl-t-                           butylketone                                                                   Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 2-(1,2,2-trimethylpropyl)-1-                             benzoylhydrazine                                                              Compound of Formula VI: Benzoylchloride                                        Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    128 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Diisopropyl ketone                                   Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of diisopropyl-                        ketone                                                                        Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 2-diisopropylmethyl-1-benzoyl                            hydrazine                                                                     Compound of Formula VI: Benzoylchloride                                        Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    129 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Cyclopropylmethyl ketone                             Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of cyclopropyl-                       methylketone                                                                   Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 2-(1-cyclopropylethyl)-1-                                benzoylhydrazine                                                              Compound of Formula VI: Benzoylchloride                                        Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    136 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Methyl-t-butylketone                                 Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of methyl-t-                           butylketone                                                                   Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 2-(1-methyl)neopentyl-1-                                 benzoylhydrazine                                                              Compound of Formula VI: 2-bromobenzoylchloride                                 Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    143 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Methyl cyclohexyl ketone                             Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of methyl                              cyclohexyl ketone                                                             Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-benzoyl-2-(1-cyclohexyl-                               ethyl)hydrazine                                                               Compound of Formula VI: benzoylchloride                                        Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    155 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Acetone                                              Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of acetone                            Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-benzoyl-2-isopropyl                                    hydrazine                                                                     Compound of Formula VI: 2,6-dichlorobenzoylchloride                            Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    156 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Trimethylacetaldehyde                                Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of trimethyl                           acetaldehyde                                                                  Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-benzoyl-2-(2,2-dimethylpropyl)                         hydrazine                                                                     Compound of Formula VI: 3,4-dichlorobenzoylchloride                            Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    157 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Pinacolone                                           Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of pinacolone                         Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-benzoyl-2-(1,2,2-trimethyl-                            propyl)hydrazine                                                              Compound of Formula VI: 4-cyanobenzoylchloride                                 Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    158 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Trimethylacetaldehyde                                Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of trimethyl                           acetaldehyde                                                                  Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-benzoyl-2-(2,2-dimethylpropyl)                         hydrazine                                                                     Compound of Formula VI: 4-ethylbenzoylchloride                                 Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    185 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Pinacolone                                           Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of pinacolone                         Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-benzoyl-2-(1,2,2-trimethyl-                            propyl)hydrazine                                                              Compound of Formula VI: 3-nitrobenzoylchloride                                 Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    186 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Trimethylacetaldehyde                                Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of trimethyl                           acetaldehyde                                                                  Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-benzoyl-2-(2,2-dimethylpropyl)                         hydrazine                                                                     Compound of Formula VI: 3-nitrobenzoylchloride                                 Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    187 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Trimethylacetaldehyde                                Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of trimethyl                           acetaldehyde                                                                  Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-benzoyl-2-(2,2-dimethylpropyl)                         hydrazine                                                                     Compound of Formula VI: 3-toluoyl chloride                                     Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    188 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Trimethylacetaldehyde                                Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of trimethyl                           acetaldehyde                                                                  Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-benzoyl-2-(2,2-dimethylpropyl)                         hydrazine                                                                     Compound of Formula VI: 4-chlorobenzoylchloride                                Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    189 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Trimethylacetaldehyde                                Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: Benzoylhydrazone of trimethyl                           acetaldehyde                                                                  Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-benzoyl-2-(2,2-dimethylpropyl)                         hydrazine                                                                     Compound of Formula VI: 2,4-dinitrobenzoylchloride                             Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    332 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: Pinacolone                                           Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoyl hydrazone of                                  pinacolone                                                                    Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(1,2,2-                                  trimethylpropyl)hydrazine                                                     Compound of Formula VI: 2-nitrobenzoylchloride                                 Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    336 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: Pinacolone                                           Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoyl hydrazone of                                  pinacolone                                                                    Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(1,2,2-                                  trimethylpropyl)hydrazine                                                     Compound of Formula VI: 3,5-dimethylbenzoylchloride                            Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    337 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: Pinacolone                                           Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoyl hydrazone of                                  pinacolone                                                                    Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(1,2,2-                                  trimethylpropyl)hydrazine                                                     Compound of Formula VI: 2-nitro-3-methyl benzoyl                                chloride                                                                      Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    338 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: Pinacolone                                           Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoyl hydrazone of                                  pinacolone                                                                    Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(1,2,2-                                  trimethylpropyl)hydrazine                                                     Compound of Formula VI: 2-nitro-5-methylbenzoyl chloride                       Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    339 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: Pinacolone                                           Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoyl hydrazone of                                  pinacolone                                                                    Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(1,2,2-                                  trimethylpropyl)hydrazine                                                     Compound of Formula VI: 3-toluoyl chloride                                     Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    340 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: Pinacolone                                           Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoyl hydrazone of                                  pinacolone                                                                    Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(1,2,2-                                  trimethylpropyl)hydrazine                                                     Compound of Formula VI: 2-iodobenzoyl chloride                                 Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    382 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: Pinacolone                                           Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoyl hydrazone of                                  pinacolone                                                                    Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(1,2,2-                                  trimethylpropyl)hydrazine                                                     Compound of Formula VI: 2-toluoyl chloride                                     Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    383 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: Pinacolone                                           Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoyl hydrazone of                                  pinacolone                                                                    Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(1,2,2-                                  trimethylpropyl)hydrazine                                                     Compound of Formula VI: 2-trifluoromethylbenzoyl                                chloride                                                                      Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    384 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: Pinacolone                                           Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoyl hydrazone of                                  pinacolone                                                                    Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(1,2,2-                                  trimethylpropyl)hydrazine                                                     Compound of Formula VI: benzoyl chloride                                       Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    399 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: 4,4-dimethyl-2-pentanone                             Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoyl hydrazone of                                  3,4-dimethyl-2-pentanone                                                      Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(4,4-                                    dimethyl-2-pentyl)hydrazine                                                   Compound of Formula VI: 3,5-dimethylbenzoyl chloride                           Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    400 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: 4,4-dimethyl-2-pentanone                             Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoyl hydrazone of                                  4,4-dimethyl-2-pentanone                                                      Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(4,4-                                    dimethyl-2-pentyl)hydrazine                                                   Compound of Formula VI: 3,4-dichlorobenzoyl chloride                           Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    414 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: 3-methyl-3-ethyl-2-pentanone                         Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoyl hydrazone of                                  3-methyl-3-ethyl-2-pentanone                                                  Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(3-methyl-3-                             ethylpent-2-yl)hydrazine                                                      Compound of Formula VI: benzoyl chloride                                       Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    415 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: 3-methyl-3-ethyl-2-pentanone                         Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoyl hydrazone of                                  3-methyl-3-ethyl-2-pentanone                                                  Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(3-methyl-3-                             ethylpent-2-yl)hydrazine                                                      Compound of Formula VI: 3,5-dimethylbenzoyl chloride                           Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    416 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: 3-methyl-3-ethyl-2-pentanone                         Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoyl hydrazone of                                  3-methyl-3-ethyl-2-pentanone                                                  Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(3-methyl-3-                             ethylpent-2-yl)hydrazine                                                      Compound of Formula VI: 2-nitrobenzoyl chloride                                Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    417 Compound of Formula VII: 4-ethylbenzoyl hydrazine                           Compound of Formula VIII: Pinacolone                                           Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-ethylbenzoyl hydrazone of                             pinacolone                                                                    Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-ethylbenzoyl)-2-(1,2,2-                             trimethylpropyl)hydrazine                                                     Compound of Formula VI: 3,5-dimethylbenzoyl chloride                           Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    418 Compound of Formula VII: 4-ethylbenzoyl hydrazine                           Compound of Formula VIII: Pinacolone                                           Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-ethylbenzoyl hydrazone of                             pinacolone                                                                    Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-ethylbenzoyl)-2-(1,2,2-                             trimethylpropyl)hydrazine                                                     Compound of Formula VI: 2-nitro-5-methylbenzoyl                                 chloride                                                                      Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    421 Compound of Formula VII: 4-ethylbenzoyl hydrazine                           Compound of Formula VIII: Acetone                                              Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-ethylbenzoyl hydrazone of                             acetone                                                                       Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-ethylbenzoyl)-2-isopropyl                           hydrazine                                                                     Compound of Formula VI: 3,5-dimethylbenzoyl chloride                           Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    434 Compound of Formula VII: 4-ethylbenzoyl hydrazine                           Compound of Formula VIII: Pinacolone                                           Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-ethylbenzoyl hydrazone of                             pinacolone                                                                    Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-ethylbenzoyl)-2-(1,2,2-                             trimethylpropyl)hydrazine                                                     Compound of Formula VI: 2,4-dichlorobenzoyl chloride                           Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    435 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: 3-methyl-3-ethyl-2-pentanone                         Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoylhydrazone of 3-methyl-                         3-ethyl-2-pentanone                                                           Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(3-methyl-                               3-ethylpent-2-yl)hydrazine                                                    Compound of Formula VI: 2-nitro-5-methylbenzoyl chloride                       Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    436 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: 3-methyl-3-ethyl-2-pentanone                         Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoylhydrazone of 3-methyl-                         3-ethyl-2-pentanone                                                           Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(3-methyl-                               3-ethylpent-2-yl)hydrazine                                                    Compound of Formula VI: 2-nitro-3-methylbenzoyl chloride                       Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    453 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: 2,2-dimethyl-3-pentanone                             Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoylhydrazone of 2,2-                              dimethyl-3-pentanone                                                          Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(2,2-dimethyl-                           pent-3-yl)hydrazine                                                           Compound of Formula VI: Benzoyl chloride                                       Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    470 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: 2,2-dimethyl-3-pentanone                             Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoylhydrazone of 2,2-                              dimethyl-3-pentanone                                                          Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(2,2-                                    dimethylpent-3-yl)hydrazine                                                   Compound of Formula VI: 2-nitrobenzoyl chloride                                Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    471 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: 2,2-dimethyl-3-butanone                              Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoylhydrazone of 2,2-                              dimethyl-3-butanone                                                           Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(2,2-                                    dimethylbut-3-yl)hydrazine                                                    Compound of Formula VI: 2-nitro-5-methylbenzoyl chloride                       Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    472 Compound of Formula VII: 4-toluoylhydrazine                                 Compound of Formula VIII: 2,2-dimethyl-3-pentanone                             Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: 4-toluoylhydrazone of 2,2-                              dimethyl-3-pentanone                                                          Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(4-toluoyl)-2-(2,2-                                    dimethylpent-3-yl)hydrazine                                                   Compound of Formula VI: 3,5-dimethylbenzoyl chloride                           Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    546 Compound of Formula VII: 2,3-dimethylbenzoyl hydrazine                      Compound of Formula VIII: Pinacolone                                           Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: (2,3-dimethylbenzoyl)hydrazone                          of pinacolone                                                                 Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(2,3-dimethylbenzoyl)-2-                               (1,2,2-trimethylpropyl)                                                        hydrazine                                                                     Compound of Formula VI: 3,5-dimethylbenzoyl chloride                           Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    547 Compound of Formula VII: 2,3-dimethylbenzoyl hydrazine                      Compound of Formula VIII: Pinacolone                                           Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula IX: (2,3-dimethylbenzoyl)hydrazone                          of pinacolone                                                                 Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Acetic acid                                                          Compound of Formula X: 1-(2,3-dimethylbenzoyl)-                                 (1,2,2-trimethylpropyl)                                                        hydrazine                                                                     Compound of Formula VI: 3-toluoyl chloride                                     Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    634 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Methyl t-butyl ketone                                Solvent: Methanol                                                              Catalyst: Hydrochloric acid                                                    Compound of Formula IX: Benzoylhydrazone of methyl                              t-butyl ketone                                                                Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Hydrochloric acid                                                    Compound of Formula X: 1-(1,2,2-trimethylpropyl)-2-                             benzoylhydrazine                                                              Compound of Formula VI: 2-methyl-3-chlorobenzoyl chloride                      Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    955 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Deoxybenzoin                                         Solvent: Methanol                                                              Catalyst: Hydrochloric acid                                                    Compound of Formula IX: Benzoylhydrazone of                                     doexybenzoin                                                                  Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Hydrochloric acid                                                    Compound of Formula X: 1-(1,2-diphenylethyl)-2-benzoyl-                         hydrazine                                                                     Compound of Formula VI: 3-toluoyl chloride                                     Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    956 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Cyclopentanone                                       Solvent: Methanol                                                              Catalyst: Hydrochloric acid                                                    Compound of Formula IX: Benzoylhydrazone of                                     cyclopentanone                                                                Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Hydrochloric acid                                                    Compound of Formula X: 1-cyclopentyl-2-benzoyl hydrazine                       Compound of Formula VI: 3-toluoyl chloride                                     Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    957 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Cyclohexanone                                        Solvent: Methanol                                                              Catalyst: Hydrochloric acid                                                    Compound of Formula IX: Benzoylhydrazone of                                     Cyclohexanone                                                                 Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Hydrochloric acid                                                    Compound of Formula X: 1-cyclohexyl-2-benzoyl hydrazine                        Compound of Formula VI: 3-toluoyl chloride                                     Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    958 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: 2-methyl cyclohexanone                               Solvent: Methanol                                                              Catalyst: Hydrochloric acid                                                    Compound of Formula IX: Benzoyl hydrazone of                                    2-methyl-cyclohexanone                                                        Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Hydrochloric acid                                                    Compound of Formula X: 1-(2-methylcyclohexyl)-2-benzoyl                         hydrazine                                                                     Compound of Formula VI: 3-toluoyl chloride                                     Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                    960 Compound of Formula VII: Benzoylhydrazine                                   Compound of Formula VIII: Phenylcyclopentyl ketone                             Solvent: Methanol                                                              Catalyst: Hydrochloric acid                                                    Compound of Formula IX: Benzoylhydrazone of phenyl-                             cyclopentylketone                                                             Reducing Agent: Sodium cyanoborohydride                                        Solvent: Methanol                                                              Catalyst: Hydrochloric acid                                                    Compound of Formula X: 1-(alpha-cyclopentylbenzyl)-2-                           benzoyl hydrazine                                                             Compound of Formula VI: 3-toluoyl chloride                                     Base: Sodium hydroxide                                                         Solvent: Toluene and water                                                  ______________________________________                                    

By following substantially the procedures in Example 220 and using the reactants shown below in Table V, the products of Examples 168, 170, 171, 172, 191, 192, 193, 213, 221 through 223, 232, 233, 293, 326, 331, 379, 397, 398, 425 and 458 were prepared.

                  TABLE V                                                          ______________________________________                                         Ex.  Compound of  Compound of                                                    No. Formula XII Formula XIII Base Solvent                                    ______________________________________                                         168  3,4-dimethoxy-                                                                              N'-t-butyl-N'-                                                                              sodium toluene                                     benzoyl chloride benzoylhydrazine hydroxide and water                         170 2-chloromethyl- N'-t-butyl-N'- sodium toluene                               benzoyl chloride benzoyl hydrazine hydroxide and water                        171 4-n-propylbenzoyl N'-t-butyl-N'- sodium toluene                             chloride benzoyl hydrazine hydroxide and water                                172 2-nitrobenzoyl N'-t-butyl-N'- sodium toluene                                chloride benzoyl hydrazine hydroxide and water                                191 3,4-dichloro- N'-t-butyl-N'- sodium toluene                                 benzoyl chloride (4-chlorobenzoyl) hydroxide and water                          hydrazine                                                                    192 4-n-heptyl- N'-t-butyl-N'- sodium toluene                                   benzoyl chloride (4-chlorobenzoyl) hydroxide and water                          hydrazine                                                                    193 4-n-propyl- N'-t-butyl-N'- sodium toluene                                   benzoyl chloride (4-chlorobenzoyl) hydroxide and water                          hydrazine                                                                    212 2-fluoro- N'-t-butyl-N'- sodium toluene                                     benzoyl chloride (4-chlorobenzoyl) hydroxide and water                          hydrazine                                                                    213 2,4-dichloro- N'-t-butyl-N'- sodium toluene                                 benzoyl chloride (4-chlorobenzoyl) hydroxide and water                          hydrazine                                                                    221 3-nitrobenzoyl N'-t-butyl-N'- sodium toluene                                chloride benzoylhydrazine hydroxide and water                                 222 2,6-dichloro- N'-t-butyl-N' sodium toluene                                  benzoyl chloride benzoylhydrazine hydroxide and water                         223 2,4-difluoro- N'-t-butyl-N'- sodium toluene                                 benzoyl chloride benzoylhydrazine hydroxide and water                         232 4-nitrobenzoyl N'-t-butyl-N'- sodium toluene                                chloride benzoylhydrazine hydroxide and water                                 233 4-cyanobenzoyl N'-t-butyl-N'- sodium toluene                                chloride benzoylhydrazine hydroxide and water                                 293 2-chloromethyl N'-t-butyl-N'- sodium toluene                                benzoyl chloride (4-chlorobenzoyl) hydroxide and water                          hydrazine                                                                    326 3-bromo-4-methyl- N'-t-butyl-N'- triethyl methylene                         benzoic methane- benzoylhydrazine amine chloride                               sulfonic anhydride                                                            331 4-fluorobenzoyl N'-t-butyl-N'- sodium toluene                               chloride benzoylhydrazine hydroxide and water                                 379 2,3-dimethyl N'-t-butyl-N'- sodium toluene                                  benzoylchloride (3-toluoyl)- hydroxide and water                                hydrazine                                                                    397 2-methyl-3-chloro- N'-t-butyl-N'- sodium toluene                            benzoyl chloride (3-toluoyl)- hydroxide and water                               hydrazine                                                                    398 2-methyl-3-chloro- N'-t-butyl-N'- sodium toluene                            benzoyl chloride benzoylhydrazine hydroxide and, water                        425 3-chloro-4-fluoro- N'-t-butyl-N'- sodium toluene                            benzoyl chloride benzoylhydrazine hydroxide and water                         458 3-chloro-4-fluoro- N'-t-butyl-N'- sodium toluene                            benzoyl chloride (3,4-dichloro- hydroxide and water                             benzoyl)hydrazine                                                          ______________________________________                                    

Example 324 but using the appropriately substituted reactants, the compounds of Examples 323 and 979 to 989 were prepared.

Using a nitrobenzoyl compound of Formula II as a reactant and reducing it, followed in certain cases by an addition reaction (such as alkylation) under the conditions (additional reactant, base or acid, and solvent) set forth in Table VI, the products of Examples 329, 330, 350 through 354, 372, 375, 473 and 484 were prepared.

                  TABLE VI                                                         ______________________________________                                         Ex.  Compound of               Base or                                           No. Formula II Reactant Acid Solvent                                         ______________________________________                                         162  N-benzoyl-N'-t-butyl-                                                                         sodium            methanol                                    N'-(4-formylbenzoyl)- borohydride                                              hydrazine                                                                     329 N-benzoyl-N'-t-butyl-N'- zinc dust  acetic                                  (3-nitrobenzoyl)-   acid                                                       hydrazine                                                                     330 N-benzoyl-N'-t-butyl-N'- zinc dust  acetic                                  (2-nitrobenzoyl)-   acid                                                       hydrazine                                                                     350 N-(2-nitro-3-methoxy- zinc dust  acetic                                     benzoyl)-N'-t-butyl-N'-   acid                                                 (3-toluoyl)hydrazine                                                          351 N-(4-nitrobenzoyl)-N'- hydrogen,  ethyl                                     t-butyl-N'-(4-chloro- platinum  acetate-                                       benzoyl)hydrazine on carbon  methanol                                         352 N-(4-aminobenzoyl)-N'- methyl pyridine methylene                            t-butyl-N'-(4-chloro- chloro-  chloride                                        benzoyl)hydrazine formate                                                     353 N-(4-aminobenzoyl)-N'- acetic                                               t-butyl-N'-(4-chloro- anhydride                                                benzoyl)hydrazine                                                             354 N-(2-nitro-3-methoxy- 1. H.sub.2 /catalyst  1. ethyl                        benzoyl)-N'-t-butyl- 2. AC.sub.2 O  acetate                                    N'-(3-toluoyl)hydrazine   2. none                                             372 N-(3-nitrobenzoyl)-N'- zinc  aqueous                                        t-butyl-N'-(3-toluoyl)- dust  acetic                                           hydrazine   acid                                                              375 N-(3-aminobenzoyl)-N'- methacryloyl sodium water                            t-butyl-N'-(3-toluoyl)- chloride hydroxide                                     hydrazine                                                                     473 N-(2-nitro-3-methoxy- zinc ammo- aqueous                                    benzoyl)-N'-t-butyl-N'- dust nium ethanol                                      benzoylhydrazine  chloride                                                    484 N-(2-methyl-3-nitro zinc ammo- aqueous                                      benzoyl)-N'-t-butyl-N'- dust nium ethanol                                      (3-toluoyl) hydrazine  chloride                                             ______________________________________                                    

Using a chloromethylbenzoyl compound of Formula II as a reactant and performing a substitution reaction under the conditions (base or acid, and solvent) set forth in Table VII, the products of Examples 159, 161, 162, 294, 361, 362, 363 and 367 were prepared.

    ______________________________________                                         Ex.  Compound of               Base or                                           No. Formula II Reactant Acid Solvent                                         ______________________________________                                         159  N-benzoyl-N'-t-butyl-N'-                                                                      sodium            N,N-                                        (3-chloromethylbenzoyl) acetate  dimethyl-                                     hydrazine   formamide                                                         161 N-benzoyl-N'-t-butyl-N'- p-thiocresol sodium toluene-                       (3-chloromethylbenzoyl)  hydroxide water                                       hydrazine                                                                     294 N-(2-chloromethyl- diethylamine  tetra-                                     benzoyl)-N"-t-butyl-   hydro-                                                  N'-(4-chlorobenzoyl)-   furan                                                  hydrazine                                                                     361 N-(4-chloromethyl sodium  N,N-                                              benzoyl)-N'-t-butyl-N'- acetate  dimethyl-                                     benzoyl hydrazine   formamide                                                 362 N-(4-chloromethyl potassium  ethanol                                        benzoyl)-N'-t-butyl-N'- thiocyanate                                            benzoyl hydrazine                                                             363 N-(4-acetoxymethyl  sodium methanol                                         benzoyl)-N'-t-butyl-N'-  hydroxide                                             benzoylhydrazine                                                              367 N-(4-chloromethyl potassium  dimethyl                                       benzoyl)-N'-t-butyl-N'- cyanide  formamide                                     benzoyl hydrazine                                                           ______________________________________                                    

Using an acetyloxybenzoyl compound of Formula II as a reactant and performing a hydrolysis, under the conditions (base and solvent) set forth in Table VIII, the products of Examples 151, 165, 203, 271, 285, 333, 349 and 614 were prepared.

                  TABLE VIII                                                       ______________________________________                                         Ex.  Compound of               Base or                                           No. Formula II Reactant Acid Solvent                                         ______________________________________                                         151  N-benzoyl-N'-t-butyl- sodium   methanol                                      N'-(2-acetoxybenzoyl)- hydroxide                                               hydrazine                                                                     165 N-benzoyl-N'-(1,2,2- sodium methanol                                        trimethylpropyl)-N'- hydroxide                                                 2-acetoxybenzoyl)hydrazine                                                    203 N-benzoyl-N'-t-butyl-N'- potassium methanol                                 (3-acetoxybenzoyl) hydroxide                                                   hydrazine                                                                     271 N-(4-acetoxybenzoyl)-N'- potassium methanol                                 t-butyl-N'-benzoyl hydroxide                                                   hydrazine                                                                     285 N-(4-acetoxybenzoyl)-N'- potassium methanol                                 t-butyl-N'-(3-toluoyl) hydroxide                                               hydrazine                                                                     333 N-(3-acetoxybenzoyl)-N'- potassium methanol                                 t-butyl-N'-benzoyl hydroxide                                                   hydrazine                                                                     349 N-(4-carbomethoxy sodium aqueous                                            benzoyl)-N'-t-butyl- hydroxide tetra-                                          N'-(3-toluoyl)hydrazine  hydro-                                                  furan                                                                       614 N,N'-bis-(2-acetoxy- sodium methanol                                        benzoyl)-N'-t-butyl hydroxide                                                  hydrazine                                                                   ______________________________________                                    

Using a hydroxybenzoyl compound of Formula II as a reactant and performing an alkylation or esterification, under the conditions (base and solvent) set forth in Table IX, the products of Examples 144, 286, 335, 345, 358, 359, 360, 365, 366 and 385 were prepared.

                  TABLE IX                                                         ______________________________________                                         Ex.  Compound of                                                                 No. Formula II Reactant Base Solvent                                         ______________________________________                                         144  N-benzoyl-N'-t-butyl-                                                                         allyl bromide                                                                             potassium                                                                             tetra-                                      N'-(4-hydroxybenzoyl)-  t-butoxide hydro-                                      hydrazine   furan                                                             286 N-(4-hydroxybenzoyl)- allyl bromide potassium tetra-                        N'-t-butyl-N'-benzoyl-  t-butoxide hydro-                                      hydrazine   furan                                                             335 N(3hydroxybenzoyl)- allyl bromide sodium dimethyl-                          N'-t-butyl-N'-benzoyl-  hydride formamide                                      hydrazine                                                                     345 N-(3-hydroxybenzoyl)- vinyl potassium tetra-                                N'-t-butyl-N'-benzoyl- chloroformate t-butoxide hydro-                         hydrazine   furan                                                             358 N-(4-hydroxybenzoyl)- chloromethyl- potassium tetra-                        N'-t-butyl-N'-benzoyl- methyl ether t-butoxide hydro-                          hydrazine   furan                                                             359 N-(4-hydroxybenzoyl)- N,N-dimethyl- potassium tetra-                        N'-t-butyl-N benzoyl- carbamoyl t-butoxide hydro-                              hydrazine chloride  furan                                                     360 N-(4-hydroxybenzoyl)- ethyl bromo- potassium tetra-                         N'-t-butyl-N'-benzoyl- acetate t-butoxide hydro-                               hydrazine   furan                                                             365 N-(4-hydroxybenzoyl)- chloromethyl- sodium dimethyl-                        N'-t-butyl-N'-benzoyl- methyl hydride formamide                                hydrazine sulfide                                                             366 N-(4-hydroxybenzoyl)- isobutyl potassium dimethyl                           N'-t-butyl-N'-benzoyl- bromide t-butoxide formamide                            hydrazine                                                                     385 N-(4-hydroxybenzoyl)- chloro- potassium tetra-                              N'-t-butyl-N'-benzoyl- methyl- t-butoxide hydro-                               hydrazine methyl  furan                                                         ether                                                                      ______________________________________                                    

Using a compound of Formula II as a reactant and performing the stated reaction under the conditions (additional reactant, base or acid, and solvent) set forth in Table X, the products of Examples 149, 164, 166, 368, 369, 373, 374, 376, 386 and 541 were prepared.

                  TABLE X                                                          ______________________________________                                         Ex.       Compound Prepared. Reactants. Reaction                                 No. Conducted and Conditions                                                 ______________________________________                                         149       N-benzoyl-N'-t-butyl-N'-(4-methane-                                     sulfonylbenzoyl)hydrazine was prepared from                                    N-benzoyl-N'-t-butyl-N'-(4-                                                    methylthiobenzoyl)hydrazine using meta-                                        chloroperbenzoic acid in methylene chloride                                    in an oxidation reaction.                                                     164 N-benzoyl-N'-t-butyl-N'-(4-carboxybenzoyl)-                                 hydrazine was prepared from N-benzoyl-N'-t-                                    butyl-N'-(4-methoxycarbonyl-                                                   benzoyl)hydrazine sodium hydroxide as a                                        base and methanol as solvent in a                                              hydrolysis reaction.                                                          166 N-benzoyl-N'-t-butyl-N'-(4-(2,2-                                            dichloroethenyl)benzoyl)hydrazine was                                          prepared from N-benzoyl-N'-t-butyl-N'-                                         (4-formylbenzoyl)hydrazine using                                               triphenylphosphine in carbon tetra-                                            chloride as solvent in a Wittig-type                                           reaction.                                                                     368 N-(4-(1,2-epoxypropyl)benzoyl)-N'-t-butyl-                                  N'-benzoylhydrazine was prepared from N-                                       (4-(1-propenyl)benzoyl)-N'-t-butyl-N'-                                         benzoylhydrazine using meta-chloroperbenzoic                                   acid in methylene chloride as solvent in an                                    oxidation reaction.                                                           369 N-(4-acetylsemicarbazone)-N'-t-butyl-                                       N-(3-toluoyl)hydrazine was prepared from N-                                    (4-acetylbenzoyl)-N'-t-butyl-N'-(3-toluoyl)                                    hydrazine using semicarbazide in ethanol                                       solvent with hydrochloric acid catalyst in                                     a condensation reaction.                                                      373 N-(4-(2-hydroxy-1,1-dimethylethylamino-                                     carbonyl)benzoyl)-N'-t-butyl-N'-(3-toluoyl)-                                   hydrazine was prepared from N-(4-                                              methoxycarbonylbenzoyl)-N'-t-butyl-N'-                                         (3-toluoyl)hydrazine using 2-amino-2-                                          methylpropanol in a condensation reaction.                                    374 N-(4-(2-hydroxyethyl)benzoyl)-N'-t-butyl-                                   N'-(3-toluoyl)hydrazine was prepared from                                      N-(4-acetylbenzoyl)-N'-t-butyl-N'-                                             (3-toluoyl)hydrazine using sodium borohydride                                  in methanol solvent in a reduction reaction.                                  376 N-(3-carboxybenzoyl)-N'-t-butyl-N'-                                         (3-toluoyl)hydrazine was prepared from                                         N-(3-cyanobenzoyl)-N'-t-butyl-N'-(3-                                           toluoyl)hydrazine using potassium hydroxide                                    as base in methanol solvent in a                                               hydrolysis reaction.                                                          386 N-(4-(1-methylethenyl)benzoyl)-N'-t-butyl-                                  N'-(3-toluoyl)hydrazine was prepared from N-                                   (4-acetylbenzoyl)-N'-t-butyl-N'-(3-toluoyl)                                    hydrazine using methyltriphenylphosphonium                                     bromide and n-butyl lithium as base and tetra-                                 hydrofuran solvent in a Wittig reaction.                                      541 N-(4-(2-hydroxyethyl)benzoyl)-N'-t-butyl-N'-                                (3,5-dimethylbenzoyl)hydrazine was prepared                                    from N-(4-(2-acetoxyethyl)benzoyl)-N'-t-butyl-                                 N'-(3,5-dimethylbenzoyl)hydrazine using sodium                                 hydroxide as base and methanol as solvent in                                   a hydrolysis.                                                               ______________________________________                                    

By following substantially the process for preparing the compounds of the present invention as described above and as exemplified by the illustrative preparation of the compounds of Examples 635 to 639 and 642 and using the appropriately substituted reactants, the compounds of Examples 640, 641 and 643 to 645 were prepared.

By following substantially the processes for preparing the compounds as described above and as exemplified by the illustrative preparation of the compounds of Examples 646, 648, 654, 656, 659 and 660 and using the appropriately substituted reactants, the compounds of Examples 647, 649 to 653, 655, 657, 658 and 661 to 681 were prepared.

By following substantially the procedures in processes described above as exemplified above by the preparation of the compounds of Examples 682, 683, 688, 689, 691, 699 and 702 and using the appropriately substituted reactants, the compounds of Examples 684 to 687, 690, 692 to 698, 700, 701, 703 to 721 and 991 were prepared.

By following substantially the procedures in the processes described above and as exemplified by the preparation of the compounds of Examples 722, 723, 724, 727, 729, 733, 737, 738, 739, 743, 754 and 755 and using the appropriately substituted reactants, the compounds of Examples 725, 726, 728, 730 to 732, 734 to 736, 740 to 742, 744 to 753, 756 and 992 were prepared.

By following substantially the procedures in the processes described above and as exemplified by the preparation of the compounds of Examples 764, 765, 766, 767, 772, 778 and 787 and using the appropriately substituted reactants, the compounds of Examples 768 to 771, 773 to 777, 779 to 786 and 788 to 794 were prepared.

By following substantially the procedures in Example 802 (without catalyst) or 809 (with catalyst) and using the reactants shown below in Table XI, the products of Examples 802 to 818 were prepared.

                  TABLE XI                                                         ______________________________________                                                           Compound                                                       Ex. Compound of of Formula Compound of                                         No. Formula VII VIIIa Formula VI                                             ______________________________________                                         802  benzoylhydrazine                                                                            acetone   benzoyl chloride                                     803 benzoylhydrazine acetone 4-chlorobenzoyl chloride                          804 4-toluoylhydrazine acetone 3-methylbenzoyl chloride                        805 benzoylhydrazine acetone 3-methylbenzoyl chloride                          806 4-chlorobenzoyl- acetone 4-chlorobenzoyl chloride                           hydrazine                                                                     807 4-toluoylhydrazine acetone 3,5-dimethylbenzoyl chloride                    808 4-toluoylhydrazine acetone 4-fluorobenzoyl chloride                        809 4-toluoylhydrazine acetone 4-methylbenzoyl chloride                        810 benzoylhydrazine methylethyl- benzoyl chloride                               ketone                                                                       811 thienoylhydrazine acetone 3-methylbenzoyl chloride                         812 4-ethylbenzoyl- acetone 3,5-dimethylbenzoyl chloride                        hydrazine                                                                     813 2-toluoylhydrazine acetone 3,5-dimethylbenzoyl chloride                    814 4-chlorobenzoyl- acetone 3-methylbenzoyl chloride                           hydrazine                                                                     815 2,4-difluorobenzoyl- acetone 4-chlorobenzoyl chloride                       hydrazine                                                                     816 2-toluoylhydrazine acetone 3-methylbenzoyl chloride                        817 2-nitrobenzoyl- acetone 3-methylbenzoyl chloride                            hydrazine                                                                     818 2-chlorobenzoyl- acetone 3-methylbenzoyl chloride                           hydrazine                                                                   ______________________________________                                    

Examples 820 and 821 were made generally in accordance with the procedures for Example 822 above.

The (trimethylsilylmethyl)hydrazine, trifluoroalkyl hydrazine and (2-carbomethoxy-2-propyl)hydrazine were made generally in accordance with the procedures from Noll, J. E.; Sprier, J. L.; Daubert, B. F.; JACS 73, 3867, 1951; Hung, S. C.; Le; Breton, G. C.; JOC 46, 5413, 1981; and Organic Synthesis Vol 5, pg. 43, respectively. From these starting materials Examples 795-801, 819 and 823-828 were made generally in accordance with the procedure for Example 822 above.

The reactants shown below in Table XII were used to prepare Examples 795-801, 819-828 and 969-978.

                  TABLE XII                                                        ______________________________________                                         Ex.  Compound of  Compound of   Compound of                                      No. Formula III Formula IV Formula VI                                        ______________________________________                                         795  2,3-dimethyl (1-methyl-2,2,2-                                                                             2,4-dichloro                                      benzoylchloride trifluoroethyl) benzoylchloride                                 hydrazine                                                                    796 2,3-dimethyl (1-methyl-2,2,2- 3,5-dimethyl                                  benzoylchloride trifluoroethyl) benzoylchloride                                 hydrazine                                                                    797 2,3-dimethyl (1-methyl-2,2,2- 2-nitro-5-                                    benzoylchloride trifluoroethyl) toluoylchloride                                 hydrazine                                                                    798 benzoylchloride (1-methyl-2,2,2- benzoylchloride                             trifluoroethyl)                                                                hydrazine                                                                    799 3,4-dichloro (2,2,2-trifluoroethyl) 3,4-dichloro                            benzoylchloride hydrazine benzoylchloride                                     800 4-chlorobenzoyl (2,2,2-trifluoroethyl) 4-chlorobenzoyl                      chloride hydrazine chloride                                                   801 benzoylchloride (2,2,2-trifluoroethyl) benzoylchloride                       hydrazine                                                                    819 benzoylchloride (1-carbmethoxy-1- benzoylchloride                            methylethyl)                                                                   hydrazine                                                                    820 4-toluoylchloride (1,1-dimethyl-3- 4-toluoylchloride                         butenyl)hydrazine                                                            821 3-toluoylchloride (1,1-dimethyl-3- 3-toluoylchloride                         butenyl)hydrazine                                                            822 benzoylchloride (1,1-dimethyl-3- benzoylchloride                             butenyl)hydrazine                                                            823 4-ethylbenzoyl (trimethylsilylmethyl) 2-nitro-5-toluoyl                     chloride hydrazine chloride                                                   824 4-chlorobenzoyl (trimethylsilylmethyl) 4-chlorobenzoyl                      chloride hydrazine chloride                                                   825 2-toluoyl (trimethylsilylmethyl) 2-toluoyl                                  chloride hydrazine chloride                                                   826 2-nitrobenzoyl (trimethylsilylmethyl) 2-nitrobenzoyl                        chloride hydrazine chloride                                                   827 benzoyl (trimethylsilylmethyl) benzoyl                                      chloride hydrazine chloride                                                   828 4-ethylbenzoyl (trimethylsilylmethyl) 3,5-dimethyl                          chloride hydrazine benzoylchloride                                            969 4-toluoyl (2-methyl-2-propenyl) benzoylchloride                             chloride hydrazine                                                            970 4-toluoyl (2-methyl-2-propenyl) 3-toluoylchloride                           chloride hydrazine                                                            971 benzoyl (1,5-dimethyl-1- 2-bromobenzoyl                                     chloride heptenyl)hydrazine chloride                                          972 benzoyl (1,5-dimethyl-1- 2-nitrobenzoyl                                     chloride heptenyl)hydrazine chloride                                          973 4-methylbenzoyl (2-bromo-2,2-dimethyl 3-toluoylchloride                     chloride ethyl)hydrazine                                                      974 4-toluoyl (1-carbethoxyethyl) benzoylchloride                               chloride hydrazine                                                            975 4-toluoyl (1-carbethoxyethyl) 2-nitrobenzoyl                                chloride hydrazine chloride                                                   976 4-toluoyl (2-dimethylamino- 3,5-dimethyl                                    chloride 1-methylethyl) benzoylchloride                                         hydrazine                                                                    977 4-toluoyl (2-hydroxy-2,2- benzoylchloride                                   chloride dimethylethyl)                                                         hydrazine                                                                    978 4-toluoyl (2-hydroxy-2,2- 3,5-dimethyl                                      chloride dimethylethyl) benzoylchloride                                         hydrazine                                                                  ______________________________________                                    

By following substantially the procedures in Examples 829, 837 and 853 and using the reactants shown in Table XIII, the products of Example Nos. 830-836, 838-852 and 854 were prepared.

                                      TABLE XIII                                   __________________________________________________________________________     Ex.                                                                              No. Halide Hydrazine Base Solvent                                            __________________________________________________________________________     830                                                                               4-chlorobenzyl                                                                          N'-t-butyl-N-benzoyl                                                                     triethylamine                                                                        dimethylformamide                                     bromide hydrazine                                                             831 2,4-dichloro- N'-t-butyl-N-benzoyl triethylamine dimethylformamide                                     benzyl bromide hydrazine                           832 3,4-dichloro- N'-t-butyl-N-benzoyl triethylamine dimethylformamide                                     benzyl bromide hydrazine                           833 4-trifluoromethyl- N'-t-butyl-N-benzoyl triethylamine dimethyl-forma                                 mide                                                  benzyl bromide hydrazine                                                      834 4-methoxycarbonyl N'-t-butyl-N-benzoyl triethylamine dimethylformami                                 de                                                    benzyl bromide hydrazine                                                      835 2-nitrobenzyl N'-t-butyl-N-benzoyl triethylamine dimethylformamide                                     bromide hydrazine                                  836 4-fluorobenzyl N'-t-butyl-N-benzoyl triethylamine dimethylformamide         bromide hydrazine                                                             838 2-bromobenzyl N'-t-butyl-N-benzoyl triethylamine dimethylformamide                                     bromide hydrazine                                  839 2-cyanobenzyl N'-t-butyl-N-benzoyl triethylamine dimethylformamide                                     bromide hydrazine                                  840 benzyl bromide N'-t-butyl-N- triethylamine dimethylformamide                                            thienoyl hydrazine                                841 4-cyanobenzyl N'-t-butyl-N-(4- triethylamine dimethylformamide                                         bromide methylbenzoyl)                               hydrazine                                                                    842 benzyl bromide N'-t-butyl-N-(4- triethylamine dimethylformamide                                         methylbenzoyl)                                      hydrazine                                                                    843 3-nitrobenzyl N'-t-butyl-N-benzoyl triethylamine dimethylformamide                                     bromide hydrazine                                  844 4-methoxybenzyl N'-t-butyl-N-benzoyl triethylamine dimethylformamide        bromide hydrazine                                                             845 3-methoxybenzyl N'-t-butyl-N-benzoyl triethylamine dimethylformamide        bromide hydrazine                                                             846 3-methylbenzyl N'-t-butyl-N-benzoyl triethylamine dimethylformamide         bromide hydrazine                                                             847 3-methylbenzyl N'-t-butyl-N-(4- triethylamine dimethylformamide                                        bromide methylbenzoyl)                               hydrazine                                                                    848 4-methylbenzyl N'-t-butyl-N-benzoyl triethylamine dimethylformamide         bromide hydrazine                                                             849 4-methylbenzyl N'-t-butyl-N-(4- triethylamine dimethylformamide                                        bromide methylbenzoyl)                               hydrazine                                                                    850 benzyl bromide N'-t-butyl-N-(3,4- triethylamine dimethylformamide                                       dichlorobenzoyl)                                    hydrazine                                                                    851 4-methylbenzyl N'-t-butyl-N-(3,4- triethylamine dimethylformamide                                      bromide dichlorobenzoyl)                             hydrazine                                                                    852 benzyl bromide N'-t-butyl-N- triethylamine dimethylformamide                                            (2-pyridinyl)                                       hydrazine                                                                    854 2-methylbenzyl N'-t-butyl-N- triethylamine dimethylformamide                                           bromide benzoyl hydrazine                        __________________________________________________________________________

By following substantially the procedures in Example 855 and using the reactants shown in Table XIV, the products of Example Nos. 856-863 were prepared.

                  TABLE XIV                                                        ______________________________________                                         Ex.                                                                              No. Hydrazone Base Solvent                                                   ______________________________________                                         856  N'-t-butyl-N'-(4-fluorobenzoyl)-                                                                  sodium      dry                                           benzaldehyde hydrazone cyanoborohydride methanol                              857 N'-t-butyl-N'-(2-bromobenzoyl)- sodium dry                                  benzaldehyde hydrazone cyanoborohydride methanol                              858 N'-t-butyl-N'-(3,4-dichloro- sodium dry                                     benzoyl) benzaldehyde hydrazone cyanoborohydride methanol                     859 N'-t-butyl-N'-(2-methylbenzoyl) sodium dry                                  benzaldehyde hydrazone cyanoborohydride methanol                              860 N'-t-butyl-N'-(3,4-dichloro- sodium dry                                     benzoyl)-3-methylbenzaldehyde cyanoborohydride methanol                        hydrazone                                                                     861 N'-t-butyl-N'-benzoyl-3-methyl- sodium dry                                  benzaldehyde hydrazone cyanoborohydride methanol                              862 N'-t-butyl-N'-2-thienoyl-3- sodium dry                                      methylbenzaldehyde hydrazone cyanoborohydride methanol                        863 N'-t-butyl-N'-benzoyl-methyl-2- sodium dry                                  pyridinylbenzaldehyde hydrazone cyanoborohydride methanol                   ______________________________________                                    

By following substantially the procedures in Example 864 and using the reactants shown in Table XV, the products of Example Nos. 865-869 were prepared.

                  TABLE XV                                                         ______________________________________                                         Ex.                                     Solvent                                  No. Benzaldehyde Halide Base Solvent System                                  ______________________________________                                         865  benzaldehyde                                                                              4-fluorobenzoyl                                                                            triethyl-                                                                            toluene                                                                              pyridine/                                  chloride amine   methylene                                                        chloride                                                                  866 benzaldehyde 3,4-dichloro- triethyl- toluene pyridine/                       benzoyl chloride amine  methylene                                                 chloride                                                                  867 benzaldehyde 2-bromobenzoyl triethyl- toluene pyridine/                      chloride amine  methylene                                                         chloride                                                                  868 3-methyl- benzoyl triethyl- toluene pyridine/                               benzaldehyde chloride amine  methylene                                             chloride                                                                  869 benzaldehyde 2-thienoyl triethyl- toluene pyridine/                          chloride amine  methylene                                                         chloride                                                                ______________________________________                                    

Example 874 was prepared by following substantially the procedures in Example 873 and using N'-t-butyl-N'-benzoylhydrazine, 3-methylbenzoyl formic acid, methanesulfonyl chloride in toluene and saturated sodium bicarbonate.

By following substantially the procedures in Example 878 and using the hydrazine shown in Table XVI and the reactants in Example 878, the products of Example Nos. 875-877 were prepared.

                  TABLE XVI                                                        ______________________________________                                         Ex.                                                                              No. Hydrazine                                                                ______________________________________                                         875           N'-t-butyl-N-(2,3-dimethylbenzoyl)                                  hydrazine                                                                     876 N'-t-butyl-N-(4-methylbenzoyl)                                              hydrazine                                                                     877 N'-t-butyl-N-(4-ethylbenzoyl)                                               hydrazine                                                                   ______________________________________                                    

By following substantially the procedure in Example Nos. 882 and 883 and using the reactants shown in Table XVII, the products of Example Nos. 879-881 and 884-886, were prepared.

                  TABLE XVII                                                       ______________________________________                                         Ex.                                                                              No. Hydrazine Base Solvent Halide                                            ______________________________________                                         879  N'-t-butyl-N-                                                                               sodium    toluene                                                                              alpha-isopropyl-4-                              (2,3-dimethyl- hydroxide  chlorophenylacetyl                                   benzoyl)hydrazine   chloride                                                  881 N'-t-butyl-N- sodium toluene phenylactyl chloride                           (4-chlorobenzoyl) hydroxide                                                    hydrazine                                                                     884 N'-t-butyl-N- sodium toluene alpha-chlorophenyl-                            (4-chlorobenzoyl) bicarbonate  acetyl chloride                                 hydrazine                                                                     885 N'-t-butyl-N- sodium toluene phenylacetyl                                   (2,3-dimethyl- hydroxide  chloride                                             benzoyl) hydrazine                                                            886 N'-t-butyl-N- sodium toluene phenylacetyl                                   (4-ethylbenzoyl) hydroxide  chloride                                           hydrazine                                                                   ______________________________________                                    

By following substantially the procedure in Example 893 and using the hydrazine and halide shown in Table XVIII and the other reactants in Example 893, the products of Example Nos. 887-892, 894-903 and 907-913 were prepared.

                  TABLE XVIII                                                      ______________________________________                                         Ex.                                                                              No. Hydrazine Halide                                                         ______________________________________                                         887   N,N'-benzoyl-N'-t-butyl hydrazine                                                                   acetyl chloride                                       888 N,N'-benzoyl-N'-t-butyl hydrazine methylchloroformate                      889 N,N'-benzoyl-N'-t-butyl hydrazine methoxyacetyl                              chloride                                                                     890 N,N'-benzoyl-N'-t-butyl hydrazine vinyl chloroformate                      891 N,N'-benzoyl-N'-t-butyl hydrazine crotonyl chloride                        892 N,N'-benzoyl-N'-t-butyl hydrazine tigloyl chloride                         894 N'-t-butyl-N-4-ethylbenzoyl-N'- methylacryloyl                              3,5-dimethylbenzoyl hydrazine chloride                                        895 N'-t-butyl-N-4-ethylbenzoyl-N'- acetyl chloride                             3,5-dimethylbenzoyl hydrazine                                                 896 N'-t-butyl-N-4-ethylbenzoyl-N'- methylchloroformate                         3,5-dimethylbenzoyl hydrazine                                                 897 N'-t-butyl-N-4-ethylbenzoyl-N'- methoxyacetyl                               3,5-dimethylbenzoyl hydrazine chloride                                        898 N'-t-butyl-N-4-ethylbenzoyl-N'- vinyl chloroformate                         3,5-dimethylbenzoyl hydrazine                                                 899 N'-t-butyl-N-4-ethylbenzoyl-N'- 2-furoyl chloride                           3,5-dimethylbenzoyl hydrazine                                                 900 N'-t-butyl-N-4-ethylbenzoyl-N'- propionyl chloride                          3,5-dimethylbenzoyl hydrazine                                                 901 N'-t-butyl-N-2,3-dimethylbenzoyl- acetyl chloride                           N'-3-methylbenzoyl hydrazine                                                  902 N'-t-butyl-N-2,3-dimethylbenzoyl- methacryloyl                              N'-3-methylbenzoyl hydrazine chloride                                         903 N'-t-butyl-N-2,3-dimethylbenzoyl- 2-furoyl chloride                         N'-3-methylbenzoyl hydrazine                                                  907 N'-t-butyl-N-4-ethylbenzoyl-N'- acryloyl chloride                           2,3-dimethylbenzoyl hydrazine                                                 908 N,N'-benzoyl-N'-t-butyl hydrazine acryloyl chloride                        909 N,N'-benzoyl-N'-t-butyl hydrazine 4-ethylbenzoyl                             chloride                                                                     910 N,N'-benzoyl-N'-t-butyl hydrazine 4-pentenoyl                                chloride                                                                     911 N,N'-benzoyl-N'-t-butyl hydrazine tigloyl chloride                         912 N'-t-butyl-N-benzoyl-N'- acetyl chloride                                    2,4-dichlorobenzoyl hydrazine                                                 913 N'-t-butyl-N-benzoyl-N'- methacryloyl                                       2,4-dichlorobenzoyl hydrazine chloride                                      ______________________________________                                    

Examples 904 and 906 were prepared by following substantially the procedures in Example 905 and using N'-t-butyl-N-(2,3-dimethylbenzoyl)hydrazine and ethanol, and N'-t-butyl-N-benzoylhydrazine and methanol, respectively.

Examples 915 and 916 were prepared by following substantially the procedures in Example 914 and using 4-methylbenzene sulfonyl and 4-fluorobenzene sulfonyl, respectively.

Examples 917 and 919-921 were prepared by following substantially the procedures in Example 918 except using the hydrazine and halide shown in Table XIX.

                  TABLE XIX                                                        ______________________________________                                         Ex.                                                                              No. Hydrazine Halide                                                         ______________________________________                                         917     N'-t-butyl-N-benzoyl hydrazine                                                                     4-fluorobenzene                                        sulfonyl chloride                                                            919 N'-t-butyl-N-benzoyl hydrazine 4-methylbenzene                               sulfonyl chloride                                                            920 N'-t-butyl-N-(2-pyridinoyl) benzene sulfonyl                                hydrazine chloride                                                            921 N'-t-butyl-N-benzoyl hydrazine 2-thienyl                                     sulfonyl chloride                                                          ______________________________________                                    

Example 1014 was prepared by following substantially the procedure in example 1013 and using mucobromic acid.

Example Nos. 999 to 1007 and 1012 were prepared by following substantially the procedure of Example 872 and using the appropriately substituted reactants.

Example Nos. 1009 to 1011 were prepared by following substantially the procedure of Example 1008 and using the appropriately substituted reactants.

It will be appreciated by those skilled in the art that compounds of Formula I can be used as precursors for preparing other compounds of Formula I by procedures well known to those skilled in the art. For example, a suitable compound of Formula I can be reduced, alkylated, substituted, esterified, hydrolyzed or the like.

As previously noted, the compounds of the present invention exhibit excellent insecticidal activity and are most active against insects of the orders Lepidoptera and Coleoptera.

In general, for the control of insects in agriculture, horticulture and forestry, the compounds of the present invention may be used at a dosage corresponding to from about 10 grams to about 10 kilograms of the active substance per hectare and from about 100 grams to about 5 kilograms per hectare of the active substance is preferred. The exact amount of dosage for a given situation can be routinely determined and depends on a variety of factors, for example, the substance used, the kind of insect, the formulation used, the state of the crop infested with the insect and the prevailing weather conditions. The term "insecticidal" as employed in the specification and claims of this application is to be construed as any means which adversely affects the existence or growth of the target insects at any stage in their life cycle. Such means can comprise a complete killing action, eradication, arresting in growth, inhibition, reducing in number, reproductive inhibition (such as ovicidal or chemisterilant) or any combination thereof. The term "control" as employed in the specification and claims of this application is to be construed as meaning "insecticidal" or protecting plants from insect damage. By "insecticidally effective amount" is meant that dosage of active substance sufficient to exert insect "control."

The compounds of the present invention, for practical applications, can be utilized in the form of compositions or formulations. Examples of the preparation of compositions and formulations can be found in the American Chemical Society publication "Pesticidal Formulation Research," (1969), Advances in Chemistry Series No. 86, written by Wade Van Valkenburg; and the Marcel Dekker, Inc. publication "Pesticide Formulations," (1973), edited by Wade Van Valkenburg. In these compositions and formulations, the active substance or substances are mixed with conventional inert agronomically acceptable (i.e., plant compatible and/or pesticidally inert) diluents or extenders such as solid carrier material or liquid carrier material, of the type usable in conventional compositions or formulations. By agronomically acceptable carrier is meant any substance which can be used to dissolve, disperse or diffuse the active ingredient in the composition without impairing the active ingredient's effectiveness and which by itself has no significant detrimental effect on the soil, equipment, desirable plants or agronomic environment. If desired, conventional adjuvants such as surfactants, stabilizers, antifoam agents and antidrift agents may also be added.

Examples of compositions and formulations according to the invention are aqueous solutions and dispersions, oily solutions and oil dispersions, pastes, dusting powders, wettable powders, emulsifiable concentrates, flowables, granules, baits, invert emulsions, aerosol compositions and fumigating candles.

Wettable powders, pastes, flowables and emulsifiable concentrates are concentrated preparation, which are diluted with water before or during use.

Baits are preparations generally comprising a food or other substance attractive to the target pest, that includes at least one lethal or non-lethal toxicant. Lethal toxicants kill the pest upon ingesting the bait while non-lethal toxicants change the behavior, feeding habits and physiology of the pest for the purpose of control.

The invert emulsions are mainly used for air application, where large areas are treated with a comparatively small amount of preparation. The invert emulsion may be prepared in the spraying apparatus shortly before, or even during, the spraying operation by emulsifying water in an oil solution or an oil dispersion of the active substance.

Compositions and formulations are prepared in a known manner, for instance by extending the active compounds with conventional dispersible liquid diluent carriers and/or dispersible solid carriers optionally with the use of carrier vehicle assistants, e.g., conventional surface-active agents, including emulsifying agents and/or dispersing agents, whereby, for example, in the case where water is used as diluent, organic solvents may be added as auxiliary solvents. The following may be chiefly considered for use as conventional carrier vehicles for this purpose: aerosol propellants which are gaseous at normal temperatures and pressures, such as halogenated hydrocarbons, e.g., dichlorodifluoromethane and trifluorochloromethane, as well as butane, propane, nitrogen and carbon dioxide; inert dispersible liquid diluent carriers, including inert organic solvents, such as aromatic hydrocarbons (e.g., benzene, toluene, xylene, alkyl naphthalenes, etc.), halogenated, especially chlorinated, aromatic hydrocarbons (e.g., chlorobenzenes, etc.), cycloalkanes (e.g., cyclohexane, etc.), paraffins (e.g., petroleum or mineral oil fractions), chlorinated aliphatic hydrocarbons (e.g., methylene chloride, chloroethylenes, etc.), vegetable oils (e.g., soybean oil, cottonseed oil, corn oil, etc.), alcohols (e.g., methanol, ethanol, propanol, butanol, glycol, etc.) as well as ethers and esters thereof (e.g., glycol monomethyl ether, etc.), amines (e.g., ethanolamine, etc.), amides (e.g., dimethyl formamide, etc.), sulfoxides (e.g., dimethyl sulfoxide, etc.), acetonitrile, ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, isophorone, etc.), and/or water; solid carriers including ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly-dispersed silicic acid, alumina and silicates; solid carriers for granules include crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks. The following may be chiefly considered for use as conventional carrier vehicle assistants: emulsifying agents, such as cationic and/or nonionic and/or anionic emulsifying agents (e.g., polyethylene oxide esters of fatty acids, polyethylene oxide ethers of fatty alcohols, alkyl sulfates, alkyl sulfonates, aryl sulfonates, albumin hydrolysates, etc., and especially alkyl arylpolyglycol ethers, magnesium stearate, sodium oleate, etc.); and/or dispersing agents, such as lignin, sulfite waste liquors, methyl cellulose, etc.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations.

If desired, it is possible to use colorants in compositions and formulations containing compounds of the present invention such as inorganic pigments, for example, iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The active compounds of the present invention may be employed alone or in the form of mixtures with one another and/or with such solid and/or liquid dispersible carrier vehicles and/or with other known compatible active agents, especially plant protection agents, such as other insecticides, arthropodicides, nematicides, fungicides, bactericides, rodenticides, herbicides, fertilizers, growth-regulating agents, synergists, etc., if desired, or in the form of particular dosage preparations for specific application made therefrom, such as solutions, emulsions, suspensions, powders, pastes, and granules which are thus ready for use.

As concerns commercially marketed preparations, these generally contemplate carrier composition mixtures in which the active compound is present in an amount substantially between about 0.1% and 99% by weight, and preferably between about 1% and 75% by weight, of the mixture. Carrier composition mixtures suitable for direct application or field application generally contemplate those in which the active compound is used in an amount substantially between about 0.0001% and 5%, preferably between about 0.001% and 3%, by weight of the mixture. Thus the present invention contemplates overall formulations and compositions which comprise mixtures of a conventional dispersible carrier such as (1) a dispersible inert finely divided carrier solid, and/or (2) a dispersible carrier liquid such as an inert organic solvent and/or water, preferably including a surface-active effective amount of a carrier vehicle assistant (e.g., a surface-active agent, such as an emulsifying agent and/or a dispersing agent), and an amount of the active compound generally, between about 0.0001% and about 99% by weight of the composition, preferably between about 0.001% and about 90% by weight of the composition, and more preferably between about 0.01% and about 75% by weight of the composition, which is effective for the purpose in question.

The active compounds can be applied as sprays by methods commonly employed, such as conventional high-gallonage hydraulic sprays, low gallonage sprays, ultra-low-volume sprays, airblast spray, aerial sprays, and dusts. If low volume applications are desired, a solution of the compound is usually used. In ultra-low-volume applications, a liquid composition containing the active compound is usually applied as a spray (e.g., mist) by means of atomizing equipment in finely divided form (average particle size of from about 50 to about 100 microns or less) using airplane crop spraying techniques. Typically only a few liters per hectare are needed and often amounts up to about 15 to 1000 g/hectare, preferably about 40 to 600 g/hectare are sufficient. With ultra-low-volume, it is possible to use highly concentrated liquid compositions with said liquid carrier vehicles containing from about 20 to about 95% by weight of the active compound.

Furthermore, the present invention contemplates methods of killing, combatting or controlling insects, which comprises contacting insects with a correspondingly combative or toxic amount (i.e., an insecticidally effective amount) of at least one active compound of the invention alone or together with a carrier vehicle (composition or formulation) as noted above. The term "contacting" as employed in the specification and claims of this application is to be construed as applying to at least one of (a) such insects and (b) the corresponding habitat thereof (i.e., the locus to be protected, for example, to a growing crop or to an area where a crop is to be grown) the active compound of this invention alone or as a constituent of a composition or formulation. The instant formulations or compositions are applied in the usual manner, for instance by spraying, atomizing, vaporizing, scattering, dusting, watering, squirting, sprinkling, pouring, fumigating, dry dressing, moist dressing, wet dressing, slurry dressing, encrusting and the like.

It will be realized, of course, that the concentration of the particular active compound utilized in admixture with the carrier vehicle will depend upon such factors as the type of equipment employed, method of application, area to be treated, types of pests to be controlled and degree of infestation. Therefore, in special cases it is possible to go above or below the aforementioned concentration ranges.

Granular preparations are produced for example, by taking up the active substance in a solvent and by using the resulting solution, as the case may be in the presence of a binder, to impregnate a granular carrier material, such as porous granules (for example, pumice and attaclay), or chopped tobacco stems or the like.

A granular preparation (frequently termed a "pellet") may alternatively be produced by compressing the active substance together with powdered minerals in the presence of lubricants and binders and by disintegrating and straining the composite to the desired grain size.

Dusts are obtainable by intimately mixing the active substance with an inert solid carrier material in a concentration of from about 1 to about 50% by weight. Examples of suitable solid carrier materials are talc, kaolin, pipe clay, diatomaceous earth, dolomite, gypsum, chalk, bentonite, attapulgite and colloidal SiO₂ or mixtures of these and similar substances. Alternatively organic carrier materials such as, for example, ground walnut shells may be used.

Wettable powders and flowables are produced by mixing from about 10 to about 99 parts by weight of a solid inert carrier such, for example, as the aforementioned carrier materials with from about 1 to about 80 parts by weight of the active substance optionally dissolved in a volatile solvent such as acetone, from about 1 to about 5 parts by weight of a dispersing agent such, for example, as the lignosulfonates or alkylnaphthalene sulfonates known for this purpose and preferably also from about 0.5 to about 5 parts by weight of a wetting agent, such as fatty alcohol sulfates, or alkylarylsulfonates of fatty acid condensation products. In the case of flowables, a liquid inert carrier such as water is also included.

To produce emulsifiable concentrates the active compound is dissolved or finely divided in a suitable solvent which preferably is poorly miscible with water, an emulsifier being added to the resulting solution. Examples of suitable solvents are xylene, toluene, high-boiling aromatic petroleum distillates, for example solvent naphtha, distilled tar oil and mixtures of these liquids. Examples of suitable emulsifiers are alkylphenoxypolyglycol ethers, polyoxyethylene sorbitan esters of fatty acids or polyoxyethylene sorbitol esters of fatty acids. The concentration of the active compound in these emulsifiable concentrates is not restricted within narrow limits and may vary between about 2% and about 50% by weight depending upon toxicant solubility. A suitable liquid highly concentrated primary composition other than an emulsifiable concentrate is a solution of the active substance in a liquid which is readily miscible with water, for example, acetone, to which solution a dispersant and, as the case may be, a wetting agent are added. When such a primary composition is diluted with water shortly before or during the spraying operation an aqueous dispersion of the active substance is obtained.

An aerosol preparation according to the invention is obtained in the usual manner by incorporating the active substance or a solution thereof in a suitable solvent in a volatile liquid suitable for use as a propellant such, for example, as a mixture of chlorine and fluorine derivatives of methane and ethane.

Fumigating candles or fumigating powders, i.e., preparations which when burning are capable of emitting a pesticidal smoke, are obtained by taking up the active substance in a combustible mixture which may, for example, comprise a sugar or a wood, preferably in the ground form, as a fuel, a substance to sustain combustion such, for example, as ammonium nitrate or potassium chlorate, and furthermore a substance for retarding combustion, for example kaolin, bentonite and/or colloidal silicic acid.

A bait preparation comprises a food or other substance attractive to pests, a carrier, the toxicant and may optionally include other substances commonly used in preparations of this kind, such as, a preservative to inhibit bacterial and fungal growth, a waterproofing agent to prevent disintegration under wet conditions and dyes or colorants as described above.

In addition to the aforementioned ingredients, the preparations according to the invention may also contain other substances commonly used in preparations of this kind.

For example, a lubricant, such as calcium stearate or magnesium stearate, may be added to a wettable powder or to a mixture to be granulated. Furthermore, there may, for example, be added "adhesives" such as polyvinylalcoholcellulose derivatives or other colloidal materials, such as casein, to improve the adherence of this pesticide to the surface to be protected.

Representative preparation of compositions and formulations including the compounds of the present invention are set forth below as Examples A through I by way of illustration but not limitation.

Example A

    ______________________________________                                         Granular                                                                             Ingredient        %/wt.                                                  ______________________________________                                         Toxicant and toxicant impurities                                                                   0.25                                                         Triton ® X-305 (binder) 0.25                                               (Octylphenyl-30-ethylene                                                       oxide ethanol)                                                                 Agsorb 24/48 (diluent) 99.50                                                   (Montmorillonite clay)                                                       ______________________________________                                    

Preparation: The toxicant and Triton® X-305 are dissolved into methylene chloride and the mixture is added to the Agsorb® with continuous mixing. The methylene chloride is then allowed to evaporate.

Example B

    ______________________________________                                         Dust                                                                                  Ingredient        %/wt.                                                 ______________________________________                                         Toxicant and toxicant impurities                                                                    1.0                                                         Talc 99.0                                                                    ______________________________________                                    

Preparation: Toxicant is dissolved in excess acetone and the mixture is impregnated onto the talc. The acetone is then permitted to evaporate.

Example C

    ______________________________________                                         Wettable Powder                                                                       Ingredient        %/wt.                                                 ______________________________________                                         Toxicant and toxicant impurities                                                                    31.3                                                        Duponal? WA Dry (wetter) 2.0                                                   (Sodium lauryl sulfate)                                                        Reax? 45A (dispersant) 5.0                                                     (Sodium lignin sulfonate)                                                      Barden clay (diluent) 31.7                                                     HiSil? 233 (diluent) 30.0                                                      (Sodium silica)                                                              ______________________________________                                    

Preparation: The toxicant, optionally dissolved in a volatile solvent, is absorbed onto the Barden clay and HiSil® carriers. The Duponal® and Reax® are then added and the entire dry mixture blended until homogeneous. The composition is then micronized to a fine particle size.

Example D

    ______________________________________                                         Emulsifiable Concentrate                                                             Ingredient          %/wt.                                                ______________________________________                                         Toxicant and toxicant impurities                                                                     15.0                                                       Sponto? 232T (emulsifier) 6.0                                                  (Anionic and nonionic blend of the                                             following surfactants: calcium                                                 dodecyl benzene sulfonate; and                                                 ethoxylated alkylphenol)                                                       Sponto? 234T (emulsifier) 4.0                                                  (Anionic and nonionic blend of the                                             following surfactants: calcium                                                 dodecyl benzene sulfonate; and                                                 ethoxylated alkylphenol)                                                       Cyclohexanone (solvent) 22.5                                                   Tenneco? 500-100 (solvent) 52.5                                                (Aromatic solvent mixture                                                      principally comprising xylene,                                                 cumene and ethyl benzene having                                                a boiling point range of 290-345° F.)                                 ______________________________________                                    

Preparation: All ingredients are mixed together with continuous agitation until a homogeneous clear solution is obtained.

Example E

    ______________________________________                                         Aerosol                                                                               Ingredient        %/wt.                                                 ______________________________________                                         Toxicant and toxicant impurities                                                                    0.5                                                         Freon 12 99.5                                                                ______________________________________                                    

Preparation: The components are mixed and packaged under pressure in a suitable container equipped with a release spray valve.

Example F

    ______________________________________                                         Fumigating Candle or Fumigating Powder                                                Ingredient        %/wt.                                                 ______________________________________                                         Toxicant and toxicant impurities                                                                    1.0                                                         Wood dust 96.0                                                                 Starch 3.0                                                                   ______________________________________                                    

Preparation: Toxicant, wood dust, and starch are blended together and then molded into a candle using a small amount of water to activate the starch.

Example G

    ______________________________________                                         Bait                                                                                 Method A                                                                   Ingredient %/wt.                                                             ______________________________________                                         Toxicant and toxicant impurities                                                                    1.00                                                        Wheat Bran (carrier and attractant) 89.95                                      Corn Syrup (attractant) 7.00                                                   Corn Oil (attractant) 2.00                                                     Kathon ® 4200 (preservative) 0.05                                          (2-n-octyl-4-isothiazolin-3-one)                                             ______________________________________                                    

Preparation: The corn oil and corn syrup are added to the wheat bran with adequate mixing. The toxicant and Kathon® are premixed with excess acetone and this solution is added to the wheat bran base with continued mixing. The acetone is then permitted to evaporate.

    ______________________________________                                         Method B                                                                         Ingredient %/wt.                                                             ______________________________________                                         Toxicant and toxicant impurities                                                                      0.06                                                      Granulated Sugar (carrier and attractant) 99.94                              ______________________________________                                    

Example H Pellet

Same as Example G, Method A, with this addition: the bait composition is formed into 1/4" diameter by 3/8" long pellets using a suitable die and press apparatus

Example I

    ______________________________________                                         Flowable                                                                              Ingredient        %/wt.                                                 ______________________________________                                         Toxicant and toxicant impurities                                                                    31.3                                                        Duponal? WA Dry (wetter) 2.0                                                   (Sodium lauryl sulfate)                                                        Reax? 45A (dispersant) 5.0                                                     (Sodium lignin sulfonate)                                                      HiSil? 233 (diluent) 30.0                                                      (Sodium silica)                                                                Kelzan? (thickener) 0.5                                                        (Xanthan gum)                                                                  Water 31.2                                                                   ______________________________________                                    

Preparation: The toxicant is absorbed onto the HiSil® carrier. The Duponal® and Reax® are then added and the entire dry mixture blended until homogeneous. The composition is then micronized to a fine particle size. The resulting powder is suspended in water and the Kelzan® added.

Compositions and formulations according to the present invention may also include known pesticidal compounds. This expands the spectrum of activity of the preparations and may give rise to synergism.

The following known insecticidal, fungicidal and acaricidal compounds are suitable for use in such a combined preparation.

Insecticides such as: achloroepoxyoctahydrodimethanonaphthalene; Carbamates, for example, N-methyl-1-naphthylcarbamate; Dinitrophenols, for example, 2-methyl-4,6-dinitrophenol and 2-(2-butyl)-4,6-dinitrophenyl-3,3-dimethylacrylate; Organic phosphorus compounds, such as dimethyl-2-methoxy-3-carbonyl-1-methylvinyl phosphate, 0,0-diethyl-0-p-nitrophenylphosphorothioate; N-monomethylamide of 0,0-dimethyldithiophosphorylacetic acid; Diphenylsulfides, for example, p-chlorobenzyl or p-chlorophenyl sulfide and 2,4,4',5-tetrachlorodiphenylsulfide; Diphenylsulfonates, for example, p-chlorophenylbenzenesulfonate; Methylcarbinols, for example, 4,4-dichloro-1-trichloromethylbenzhydrol; Quinoxaline compounds, such as methylquinoxaline dithiocarbonate; Amidines such as N'-(4-chloro-2-methylphenyl) N,N-dimethylformamidine; Pyrethroids such as Allethrin; Biologicals such as Bacillus thuringiensis preparations; Organic tin compounds such as tricyclohexyltin hydroxide; Synergists such as piperonyl butoxide; Insect growth regulators such as N-benzoyl-phenyl ureas, for example, diflubenzuron.

Fungicides such as: Organic mercury compounds, for example, phenylmercuryacetate and methylmercurycyanoguanide; Organic tin compounds, for example, triphenyltin hydroxide and triphenyltin acetate; Alkylenebisdithiocarbamates, for example, zinc ethylenebisthiocarbamate and manganese ethylenebisdithiocarbamate; and 2,4-dinitro-6-(2-octyl-phenylcrotonate), 1-bis(dimethylamino)phosphoryl-3-phenyl-5-amino-1,2,4-triazole, 6-methylquinoxaline-2,3-dithiocarbonate, 1,4-dithioanthraquinone-2,3-dicarbonitrile, N-trichloromethylthiophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide, N-dichlorofluoromethylthio-N-phenyl-N'-dimethylsulfonyldiamide and tetrachloroisophthalonitrile.

Biological Activity

It has been found by biological evaluation that compounds according to the present invention have pesticidal activity and are capable of controlling larvae and adult forms of pests, especially insects from the orders Lepidoptera and Coleoptera and most especially insects from the order Lepidoptera. One skilled in the art will know how to determine the activity of a given compound against a given insect and the dosage required to obtain general or selective insecticidal effects. The compounds of the present invention in part affect the normal development of insects, particularly insects from the order Lepidoptera, by directly and/or indirectly influencing the moulting process.

As previously noted, the compounds of the present invention are particularly suitable for controlling plant destructive insects in crops of cultivated plants, such as, but not limited to, cotton, vegetables, corn and other cereals and the like; forestry, such as, but not limited to, birch, spruce, pine, fir and the like; and ornamental plants, flowers and trees. Compounds of the present invention are also particularly suitable for controlling insects destructive to stored commodities such as seeds and the like; fruit crops, such as, but not limited to fruit and/or citrus trees, raspberry bushes and the like; and turf, such as, but not limited to, lawns, sod and the like.

In evaluating the pesticidal activity of the compounds of this invention, the following test procedures were employed.

Unless a different application rate is indicated in Table XX, a test solution containing 600 parts per million (ppm) was made by dissolving the test compound in a solvent (acetone:methanol, 1:1), adding water to give an acetone:methanol:water system of 5:5:90 and then a surfactant. A 1:1 mixture of an alkylarylpolyetheralcohol (sold under the trademark Triton® X-155) and a modified phthalic glycerol alkyl resin (sold under the trademark Triton® B-1956) was utilized at the equivalent of 1 ounce per 100 gal. of test solution as a surfactant.

Initial evaluations were made on one or more of the following pests:

    ______________________________________                                         Code                                                                             Symbol    Common Name    Latin Name                                          ______________________________________                                         SAW     Southern Armyworm                                                                             Spodoptera eridania                                       MBB Mexican Bean Beetle Epilachna varivestis                                   BW Boll Weevil Anthonomus grandis grandis                                    ______________________________________                                    

For the foliar bean beetle and armyworm tests, individual bean (Phaseolus limensis var. Woods' Prolific leaves are placed on moistened pieces of filter paper in Petri dishes. The leaves are then sprayed with the test solution using a rotating turntable and allowed to dry. The dishes are infested with 10 third instar larvae of Southern armyworm or Mexican bean beetle. The dishes are then covered.

For the Boll Weevil test ten adult weevils are placed in a 0.5 pint glass Mason jar containing a small cube of apple. The weevils are confined to the jars by fiberglass screen mesh secured by a screw-type rim cap. The jars are then sprayed with the test solution using a rotating turntable, directing the spray through the mesh into the jar.

The rotating turntable consists of a fixed, continuously operating spray nozzle under which targets are rotated at a fixed speed and distance. If the target is a Petri dish (such as for the armyworm), the distance from the nozzle is 15 inches. If the target is a Mason jar, the distance between the screened lid and the nozzle is 6 inches (10 inches from the base of the jar to the nozzle). The nozzle is located 8 inches from the rotating shaft. The targets on individual platforms revolve around the shaft at 1 revolution per 20 seconds but only a brief portion of this time occurs in the spray path. Targets pass only once under the nozzle and then are removed to drying hoods.

The nozzle used is a 1/4 JCO Spraying Systems (Wheaton, Ill.) air atomizing nozzle equipped with a No. 2850 fluid cap and No. 70 air cap. At the 10 psig air pressure used and with liquid siphon feed 0.5 GPH (gallons per hour) are delivered in a round spray pattern with a 21° spray angle. Targets are misted with spray droplets to the point that the droplets coalesce to form a uniform thin film insufficient to drown test organisms.

All treatments are maintained at 75-80° F. under continuous fluorescent light in a well-ventilated room.

For soil treatment (systemic) trials, a portion of the 600 ppm test solution is diluted to 150 ppm. Ten (10) ml of the 150 ppm test solution is pipetted into soil (approximately 200 g of standard greenhouse soil) in a 3-inch pot containing a lima bean seedling. This results in a soil concentration of approximately 8 ppm. Treated plants are maintained under existing greenhouse conditions for one week. Two bean leaves are removed and placed individually on moist filter paper in Petri dishes. One leaf is infested with 10 third instar larvae of Mexican bean beetle. The other leaf is infested with 10 third instar larvae of Southern armyworm. The dishes are then covered and held for 3 days at which time the percent control (mortality) is determined. A second observation may be made 6 days after infesting the dishes if the experimenter feels the effect may not be complete or moribund insects appear to evidence signs of some recovery. Where necessary, untreated bean leaves are introduced into dishes held for a second observation to preclude insect starvation.

The results of the initial insecticidal evaluations are given in Table XX.

Armyworm and bean beetle spray (foliar) results are 96 hour observations unless otherwise noted. Boll weevil spray results are 48 hour observations unless, in the discretion of the experimenter, particular evaluations were held for 96 hour observations if it is believed the effect of a test compound may not be complete or moribund insects appear to evidence some signs of recovery. If, after 96 hours, there was a change in the percent control, it is shown in parentheses. Soil treatment results are 72 hour observations. At the discretion of the experimenter, particular evaluations were held for 144 hour observations. If, after 144 hours, there was a change in the percent control, it is shown in parentheses. Evaluations are based on a scale of 0-100 percent in which 0 equals no activity and 100 equals total kill.

                  TABLE XX                                                         ______________________________________                                         Initial Biological Evaluations                                                           Foliar Application    Soil Application                                 Ex. Test Species Test Species                                                No.   SAW        MBB      BW      MBB   SAW                                    ______________________________________                                          1     100.sup.a  0       0       80    0                                         2 100  0 0 20 0                                                                3 100  60.sup.a 0 100 100                                                      4 100  0 0 60 0                                                                5 100  0 0 50 0                                                                6  40  0 0 --.sup.b --                                                         7 100  0 0 50 0                                                                8  10  0 0 -- --                                                               9 100  0 0 70 100                                                              10 100  0 0 60 0                                                               11 100  0 0 20 100                                                             12   20.sup.d 100  0 50 0                                                      13 100  0 0 20 100                                                             14   20.sup.d   0.sup.d 60.sup.d  0.sup.d 0.sup.d                              15 100  0 0 20 0                                                               16 100  0 0 30 100                                                             17 100  0 0 40 100                                                             18 100 100  0 100 100                                                          19 100  0 100  20 0                                                            20 100  0 0 -- --                                                              21 100  0 0 -- --                                                              22 100  0 0 40 100                                                             23 100  0 100  -- --                                                           24 100  0 80  -- --                                                            25 100  0 0 -- --                                                              26 100 100  0 0 100                                                            27  100.sup.d   0.sup.d 20.sup.d  20(40).sup.d 70.sup.d                        28  10  0 0 -- --                                                              29 100  0 0 0 40                                                               30 100  0 0 0 10                                                               31 100 100  0 40 100                                                           32   0.sup.d   20a,c 20.sup.c  -- --                                           33 100 40 0 20 0                                                               34 100 20 0 70 100                                                             35 100 100  0 100 100                                                          36 100 100  20  90 100                                                         37 100  0 0 -- --                                                              38 100 90 20  0(60) 100                                                        39 100  0 0 0 20                                                               40  40 20 20  0 0                                                              41 100  0 20  20 100                                                           42 100 100  0 100 100                                                          43 100 100  0 100 100                                                          44 100 10 0 0(20) 0                                                            45 100  0 0 0(40) 0(40)                                                        46 100  0 60  40(80) 60(80)                                                    47 100 100  0 80(90) 100                                                       48 100 100       0(40) 40(60) 100                                              49 100 100  .sup.    40(80) 10(60) 100                                         50 100  0 .sup.    40(80) 40(70) 0(10)                                         51 100 100  0 70(100) 30                                                       52 100 100  0 20(30) 20(50)                                                    53 100  0 40  20(60) 100                                                       54 100 20 0 0 0                                                                55 100 10 0 0 0                                                                56 100 100  0 60(80) 100                                                       57 100  0 0 40(60) 0                                                           58 100 20 0 20 0                                                               59 100 70 20  20 100                                                           60 100 40 0 0 0                                                                61   80.sup.d  0 0 60(80) 0                                                    62 100 40 0 20 100                                                             63 100 10 0 20 0                                                               64 100 20 0 0(100) 10(50)                                                      65 100 20 0 0(40) 100                                                          66 100 70 0 40(80) 40(50)                                                      67 100 40 0 20(80) 100                                                         68 100 10 20  20 0                                                             69 100 40 0 20 0                                                               70 100 40 20  0(20) 0                                                          71  100.sup.c 60 0 0(20) 0                                                     72  60  0 0 20 0                                                               73 100 100  0 40(80) 100                                                       74 100 80 0 20 0                                                               75 100 60 0 0 0                                                                76 100 60 0 0(20) 0                                                            77 100 100  0 0 0                                                              78  90 40 0 20 0                                                               79   0.sup.d  0 20  0 0                                                        80   20.sup.d  0 20  0 0                                                       81 100  0 20  0 20                                                             82 100  0 0 0 0                                                                83 100 100  0 60(100) 100                                                      84  10  0 0 0 0                                                                85 100 30 0 0 20                                                               86 100 30 20  0 80(100)                                                        87 100 40 40  0 40(50)                                                         88 100 20 0 0 0                                                                89 100  0 0 0 100                                                              90 100  0 0 0 90                                                               91   100a,c  0 40  0 0                                                         92 100 50 0 0 90(100)                                                          93 100  0 0 0 0                                                                94   0.sup.d 10 0 0 0                                                          95 100 100  20  40(100) 100                                                    96 100 30 0 0 0                                                                97 100  0 20  0 0                                                              98 100  0 0 0 100                                                              99 100 60 0 40(80) 100                                                        100 100 100  0 80(100) 100                                                     101 100  0 0 20 0                                                              102 100  0 0 20 0(40)                                                          103 100 100  0 0(60) 100                                                       104 100  0      0(20) 0 40(100)                                                105 100  0 40  0 100                                                           106  80  0 60  0 0(100)                                                        107 100  0 0 0(40) 100                                                         108 100  0 0 0 0                                                               109 100 20 0 0(100) 100                                                        110 100 70 0 100 90(100)                                                       111 100 100  0 0 0                                                             112 100 100  20  20(40) 90(100)                                                113 100 100  0 100 100                                                         114 100  0 0 0 10                                                              115 100 100  0 20(60) 90(100)                                                  116 100 10 0 0 0                                                               117 100 10 0 40(80) 100                                                        118 100 10 0 0 90(100)                                                         119 100  0 0 0 0                                                               120 100 30 20  0 0                                                             121 100 100  0 20(40) 100                                                      122  70 20 0 0 20(50)                                                          123 100  0 0 0(100) 100                                                        124 100 100  0 0 20(30)                                                        125 100  0 0 0 0                                                               126 100 10 0 0 0                                                               127 100 10 0 20 0                                                              128 100  0 0 0 0                                                               129 100 40 .sup.    40(60) 100(80) 80(100)                                     130 100  0 0 0(20) 100                                                         131 100  0 0 0 100                                                             132 100  0 0 20(40) 0                                                          133 100 10 0 0 0                                                               134 100 10 0 0 10(30)                                                          135 100  0 0 20(40) 60                                                         136 100 70 0 20 30(50)                                                         137 100 10 0 40(60) 0                                                          138 100  0 0 0 90(100)                                                         139 100  0 0 0(20) 0                                                           140 100  0 0 20 0                                                              141 100 100  0 20(100) 100                                                     142 100  0 0 20 40                                                             143   0.sup.d  0 0 20 0                                                        144   0.sup.d   10a,c 20.sup.c  0 0                                            145   30.sup.c  0  0.sup.c 0 0                                                 146 100 20 .sup.    40(60) 0 0                                                 147   0.sup.d  20.sup.d 20.sup.d  0.sup.d 0.sup.d                              148   60.sup.d  0 40  0 20(0)                                                  149   20.sup.c   20a,c  0.sup.c 0 0                                            150   20.sup.c  0  0.sup.c 0 0                                                 151  0  0 0 0 0                                                                152 100  0 0 0 0                                                               153 100  0 0 0 80(90)                                                          154 100 10 0 0 0                                                               155   0.sup.d 30 0 0(20) 0                                                     156   10.sup.c  0  0.sup.c 0 0                                                 157   0.sup.d 10 20  0 0                                                       158  20  0 0 0 0                                                               159  10  0 0 0 0                                                               160   20.sup.d  0 0 20 0                                                       161  30  0 0 0(20) 0                                                           162  70 20 0 40(60) 0                                                          163  20 20 0 0(20) 0                                                           164 100.sup.d  0 20  40 0                                                      165   20.sup.c 10 0 0 0                                                        166  10 10 0 0 0                                                               167  30  0 0 0 0                                                               168  10 40 0 0 0                                                               169   0.sup.d 30 0 0 0                                                         170   0.sup.d 10 0 0 0                                                         171 100 40 0 0 0                                                               172 100  0 0 0 0                                                               173  60 30 20  0 0                                                             174 100  0 0 0 80(100)                                                         175 100  0 0 0 0                                                               176   0.sup.d 10 0 0 0                                                         177 100 30 0 0 10                                                              178 100 10 0 0 10                                                              179  90  0 20  0 0                                                             180 100  0 0 0 0                                                               181 100 10 0 0 0                                                               182 100  0 0 0 0                                                               183  30 80 0 0(100) 0(100)                                                     184 100 10 0 0 0                                                               185   30.sup.c   20a,c  0.sup.c 0 0                                            186   30.sup.c  10.sup.d 30.sup.d  20.sup.d 0.sup.d                            187 100  0 0 0(20) 0(10)                                                       188  100.sup.c  0  0.sup.c 0 0                                                 189  100.sup.c  0 20  0 0                                                      190 100  0 0 0(40) 20(60)                                                      191  90  0 0 0 0                                                               192  20  0 0 0 0                                                               193 100  0 0 0 0                                                               194 100 80 20  20(60) 100                                                      195 100 80 0 80(100) 100                                                       196 100  0 0 0 100                                                             197 100  0 20  0(20) 100                                                       198 100  0 0 20 90(100)                                                        199  20 10 0 20 30                                                             200 100  0 0 0(20) 90                                                          201 100  0      0(60) 0 20(30)                                                 202  40 20 0 40 0                                                              203  60  0 .sup.    20(60) 0 0                                                 204  50  0 0 0 0                                                               205 100 10 0 20 100                                                            206 100 10 0 0 100                                                             207   0.sup.d  20.sup.d 20.sup.d  0.sup.d 0(10).sup.d                          208 100  0 0 0(20) 90                                                          209 100 10 0 60(20) 100                                                        210   20.sup.c 10 40  0 0                                                      211  20 10 0 0 0                                                               212 100  0 0 0 90(100)                                                         213 100  0 40  0 0                                                             214 100  0 0 0 40(60)                                                          215 100 10 0 0(20) 100                                                         216 100  0 20  20 50(60)                                                       217 100 60 0 20 100                                                            218  90 10 0 0 0                                                               219   60.sup.c   0.sup.c  0.sup.c 0 0                                          220 100  0 0 0 100                                                             221  60 10 0 20 0                                                              222 100   10a,c  0.sup.c 0 0                                                   223 100 10 0 40 100                                                            224  40 10 20  0 0                                                             225 100 20 0 0(20) 100                                                         226 100 10 0 0 0                                                               227 100  0 0 0 30(40)                                                          228 100  0 20  0(40) 100                                                       229  60 20 0 0 0                                                               230 100 50 0 60(80) 100                                                        231  60 20 0 40 60                                                             232 100  0 0 20 0                                                              233 100  0 0 40 60                                                             234 100 10 0 0 100                                                             235 100 60 0 100 100                                                           236 100 10 0 0 30                                                              237 100 20 0 0 0                                                               238  90 60 0 0 0                                                               239 100  0 0 0 0                                                               240  30 10 0 0 0                                                               241 100  0 0 0 0                                                               242  50 30 0 0 0                                                               243  10 20 0 0 0                                                               244 100  0 0 0 70(80)                                                          245 100  0 0 0 80(90)                                                          246 100 10 0 0 0                                                               247 100  0 0 0 0                                                               248 100  0 0 0 0                                                               249 100  0 0 0 0                                                               250  80 50 0 0 10                                                              251 100 20 20  20(40) 60                                                       252 100  0 0 0(20) 100                                                         253 100 10 .sup.    20(40) 0 20(30)                                            254 100  0 0 0 0                                                               255 100 100  0 0 0                                                             256 100  0 0 0 0                                                               257 100  0 0 20 20                                                             258  40.sup.c 90 40  100 0                                                     259 100 10 0 0 0                                                               260 100 20 0 0 0                                                               261   0.sup.d 10 0 0 0                                                         262  60  0 0 0 0                                                               263 100 30 0 20 40                                                             264  80  0      80(100) 0 10(30)                                               265   0.sup.c 10 0 0 0                                                         266   0.sup.d 10 0 0 0                                                         267 100  0 0 0 0                                                               268  40  0 0 0                                                                 269 100  0 .sup.    60(80) 0 0                                                 270 100  0 0 20(40) 0                                                          271 100 10 0 20(0) 70                                                          272  40 10 0 0 0                                                               273 100  0      40(100) 0 0                                                    274 100  0 0 20 50(90)                                                         275   40.sup.c   30a,c  0.sup.c 0 0                                            276 100 10 .sup.    20(60) 0 0                                                 277 100 30 0 20 0                                                              278  60  0 0 0 0                                                               279 100 10 0 0 0                                                               280 100 10 .sup.    20(80) 0 0                                                 281 100  0 0 0 0                                                               282 100 30 0 0 0                                                               283 100  0 0 0 0                                                               284  90 50 0 0 0                                                               285 100 50 0 0 0                                                               286 100  0 0 0 0                                                               287 100 10 0 0 0                                                               288 100  0 0 0 0                                                               289 100 40 0 20 0                                                              290 100 50 0 0 0                                                               291 100 30 0 0 80(90)                                                          292 100 10 0 0 100                                                             293  20 30 20  0 0                                                             294   0.sup.d   10a,c  0.sup.c 0 0                                             295 100 100  0 0 60(80)                                                        296 100 50 0 60(100) 100                                                       297 100 40 0 0 0                                                               298  80 30 0 0 0                                                               299 100 20 0 0 0                                                               300 100  0 0 0(20) 100                                                         301 100  0 0 0 70(100)                                                         302 100  0 0 0 0                                                               303 100 30 0 0 0                                                               304  70 90 0 0 0                                                               305 100 40 0 0 60(100)                                                         306 100 40 0 0 0                                                               307 100 60 0 0 0                                                               308   0.sup.d 40 0 0 0                                                         309 100 60 0 0 0                                                               310 100 40 0 0 0                                                               311 100 100  0 40(60) 90(100)                                                  312 100  0 0 0 10                                                              313 100 20 0 0 0                                                               314 100  0 0 0 0                                                               315 100  0 0 20(40) 0                                                          316 100  0 0 20 100                                                            317 100 20 0 0 80(100)                                                         318 100 20 0 0 90(100)                                                         319 100 20 0 0 100                                                             320 100  0 0 40 0                                                              321  80  0 0 -- --                                                             322 100  0 0 -- --                                                             323 100 20 0 -- --                                                             324 100 20 0 -- --                                                             325 100 10 0 -- --                                                             326 100 30 0 -- --                                                             327  30 30 0 -- --                                                             328   0.sup.d 50 0 -- --                                                       329 100 30 0 -- --                                                             330 100 30 0 -- --                                                             331 100 30 0 -- --                                                             332 100 70 0 -- --                                                             333  30  0 0 -- --                                                             334 100  0 0 -- --                                                             335  90 70 0 -- --                                                             336 100 30 0 -- --                                                             337   50.sup.c 30 0 -- --                                                      338 100 40 0 -- --                                                             339 100  0 .sup.    20(80) -- --                                               340 100  0 0 -- --                                                             341 100 100  0 -- --                                                           342 100  0 0 -- --                                                             343 100 10 .sup.    20(60) -- --                                               344  0.sup.c  0 40  -- --                                                      345  20  0 0 -- --                                                             346   40.sup.c   10a,c  0.sup.c -- --                                          347 100 20 0 -- --                                                             348  100.sup.c  0  0.sup.c -- --                                               349  60  0 0 -- --                                                             350 100 20 0 -- --                                                             351 100  0 0 -- --                                                             352  50 20 0 -- --                                                             353 100  0 0 -- --                                                             354 100 30 0 -- --                                                             355  100.sup.c 90 0 -- --                                                      356   40.sup.c  0  0.sup.c -- --                                               357 100 20 0 -- --                                                             358 100  0 0 -- --                                                             359 100  0 0 -- --                                                             360  70.sup.c  0  0.sup.c -- --                                                361 100 10 0 -- --                                                             362 100 70 0 -- --                                                             363 100 20 0 -- --                                                             364 100 10 0 -- --                                                             365 100  0 0 -- --                                                             366 100 40 0 -- --                                                             367 100 30 0 -- --                                                             368 100  0 0 -- --                                                             369 100  0 0 -- --                                                             370  30 30 0 -- --                                                             371 100 10 20  -- --                                                           372  30  0 0 -- --                                                             373  90 10 0 -- --                                                             374 100 10 0 -- --                                                             375  100.sup.d 10 0 -- --                                                      376  100.sup.c 20 0 -- --                                                      377 100 20 0 -- --                                                             378 100 20 0 -- --                                                             379 100 20 0 -- --                                                             380 100 10 0 -- --                                                             381 100 30 0 -- --                                                             382 100  0 20  -- --                                                           383 100 20 0 -- --                                                             384  80 20 0 -- --                                                             385 100 100  0 -- --                                                           386 100 20 20  -- --                                                           387 100  0 0 -- --                                                             388 100 30 .sup.    20(40) -- --                                               389   0.sup.d 70 0 -- --                                                       390 100 30 0 -- --                                                             391 100  0 .sup.    20(60) -- --                                               392 100 100  0 -- --                                                           393 100 20 0 -- --                                                             394 100  0 0 -- --                                                             395 100 70 0 -- --                                                             396 100 100  0 -- --                                                           397 100  0 0 -- --                                                             398 100 40 0 -- --                                                             399 100  0 0 -- --                                                             400  90  0 0 -- --                                                             401 100 70 0 -- --                                                             402 100 40 0 -- --                                                             403 100  0 0 -- --                                                             404 100 20 .sup.    20(40) -- --                                               405 100 10 0 -- --                                                             406 100  0 20  -- --                                                           407 100 20 0 -- --                                                             408  90 60 0 -- --                                                             409  40  0 0 -- --                                                             410 100 90 0 -- --                                                             411 100 10 0 -- --                                                             412  30 30 0 -- --                                                             413 100 10 0 -- --                                                             414  60 50 40  -- --                                                           415  60 20 .sup.    20(60) -- --                                               416 100 30 0 -- --                                                             417 100 20 0 -- --                                                             418 100  0 20  -- --                                                           419 100 10 0 -- --                                                             420 100  0 40  -- --                                                           421 100 10 0 -- --                                                             422 100  0 0 -- --                                                             423 100  0 0 -- --                                                             424 100 10 0 -- --                                                             425 100 70 0 -- --                                                             426 100  0 0 -- --                                                             427 100 20 0 -- --                                                             428 100 10 .sup.    20(80) -- --                                               429 100 20 0 -- --                                                             430 100  0 0 -- --                                                             431  90 40 0 -- --                                                             432 100 20 0 -- --                                                             433 100  0 0 -- --                                                             434 100 10 20  -- --                                                           435 100 20 0 -- --                                                             436   0.sup.d 30 0 -- --                                                       437 100 10 0 -- --                                                             438 100 40 0 -- --                                                             439 100  0 0 -- --                                                             440 100 20 0 -- --                                                             441 100 20 0 -- --                                                             442 100 30 0 -- --                                                             443 100 20 0 -- --                                                             444 100  0 0 -- --                                                             445 100 20 0 -- --                                                             446 100 20 20  -- --                                                           447 100 20 0 -- --                                                             448 100 20 0 -- --                                                             449 100 20 0 -- --                                                             450 100 20 0 -- --                                                             451 100 50 0 -- --                                                             452 100 30 0 -- --                                                             453 100 30 0 -- --                                                             454 100  0 0 -- --                                                             455 100 50 0 -- --                                                             456 100 20 0 -- --                                                             457 100 50 0 -- --                                                             458 100  0 0 -- --                                                             459 100  0 20  -- --                                                           460 100  0 0 -- --                                                             461   0.sup.d   10a,c  0.sup.c -- --                                           462  40 20 0 -- --                                                             463  50 10 0 -- --                                                             464 100 10 0 -- --                                                             465  70  0 0 -- --                                                             466 100  0 40  -- --                                                           467 100  0 0 -- --                                                             468 100 10 0 -- --                                                             469  60.sup.c 20 0 -- --                                                       470 100 10 0 -- --                                                             471 100 10 0 -- --                                                             472 100  0 0 -- --                                                             473 100 20 0 -- --                                                             474  100.sup.c 20 0 -- --                                                      475   50.sup.c  0  0.sup.c -- --                                               476 100  0 0 -- --                                                             477 100 10 20  -- --                                                           478 100 20 0 -- --                                                             479 100  0 0 -- --                                                             480 100 20 0 -- --                                                             481 100  0 0 -- --                                                             482 100 20 0 -- --                                                             483 100 10 0 -- --                                                             484 100 20 0 -- --                                                             485 100 40 0 -- --                                                             486 100 20 0 -- --                                                             487 100 50 0 -- --                                                             488 100  0 0 -- --                                                             489 100 40 20  -- --                                                           490 100  0 0 -- --                                                             491  60 20 0 -- --                                                             492 100  0 0 -- --                                                             493 100 20 0 -- --                                                             494 100  0 0 -- --                                                             495 100 10 0 -- --                                                             496 100  0 0 -- --                                                             497 100 10 0 -- --                                                             498 100  0 .sup.    60(80) -- --                                               499 100 40 0 -- --                                                             500 100 10 0 -- --                                                             501 100 30 0 -- --                                                             502 100 10 20  -- --                                                           503  90 30 0 -- --                                                             504 100 40 0 -- --                                                             505 100 30 20  -- --                                                           506 100  0 0 -- --                                                             507  60 20 0 -- --                                                             508 100  0 0 -- --                                                             509 100 70 0 -- --                                                             510 100 10 0 -- --                                                             511 100 10 0 -- --                                                             512  90 20 0 -- --                                                             513 100 10 0 -- --                                                             514 100 30 0 -- --                                                             515 100 100  0 -- --                                                           516 100 10 0 -- --                                                             517 100 10 0 -- --                                                             518 100 30 0 -- --                                                             519 100 10 0 -- --                                                             520 100 30 0 -- --                                                             521 100 50 0 -- --                                                             522 100 10 0 -- --                                                             523 100 10 0 -- --                                                             524  90 30 0 -- --                                                             525 100 30 0 -- --                                                             526 100 10 0 -- --                                                             527 100  0 0 -- --                                                             528 100  0 0 -- --                                                             529 100 10 0 -- --                                                             530 100 10 0 -- --                                                             531 100 10 0 -- --                                                             532 100 20 0 -- --                                                             533 100  0 0 -- --                                                             534 100 10 0 -- --                                                             535 100  0 0 -- --                                                             536 100 10 0 -- --                                                             537 100  0 0 -- --                                                             538 100 20 0 -- --                                                             539 100  0 0 -- --                                                             540 100 10 0 -- --                                                             541 100  0 0 -- --                                                             542 100  0 0 -- --                                                             543 100  0 0 -- --                                                             544 100  0 0 -- --                                                             545 100  0 0 -- --                                                             546 100  0 0 -- --                                                             547 100  0 0 -- --                                                             548 100 30 20  -- --                                                           549 100 30 0 -- --                                                             550 100 40 0 -- --                                                             551 100  0 0 -- --                                                             552 100 30 20  -- --                                                           553 100 40 0 -- --                                                             554 100 20 0 -- --                                                             555 100 20 0 -- --                                                             556 100 10 0 -- --                                                             557  30 30 0 -- --                                                             558 100 20 0 -- --                                                             559 100 50 0 -- --                                                             560  90  0 0 -- --                                                             561 100 30 20  -- --                                                           562 100  0 0 -- --                                                             563 100 10 0 -- --                                                             564 100  0 0 -- --                                                             565 100  0 0 -- --                                                             566  40 70 0 -- --                                                             567 100 40 20  -- --                                                           568 100  0 0 -- --                                                             569 100 20 0 -- --                                                             570 100 10 0 -- --                                                             571 100 50 0 -- --                                                             572 100 80 0 -- --                                                             573 100 20 0 -- --                                                             574 100  0 0 -- --                                                             575 100  0 20  -- --                                                           576 100 20 0 -- --                                                             577 100  0 0 -- --                                                             578 100 40 0 -- --                                                             579 100 40 0 -- --                                                             580 100  0 0 -- --                                                             581 100  0 0 -- --                                                             582 100  0 0 -- --                                                             583 100 30 0 -- --                                                             584 100  0 0 -- --                                                             585 100  0 0 -- --                                                             586 100  0 0 -- --                                                             587 100 10 0 -- --                                                             588 100 40 0 -- --                                                             589 100 40 0 -- --                                                             590 100 30 0 -- --                                                             591 100  0 0 -- --                                                             592 100 40 0 -- --                                                             593 100 40 0 -- --                                                             594 100 10 0 -- --                                                             595 100 10 20  -- --                                                           596 100 80 0 -- --                                                             597 100 40 0 -- --                                                             598 100 10 20  -- --                                                           599 100 40 0 -- --                                                             600 100 30 0 -- --                                                             601 100 10 0 -- --                                                             602 100 10 0 -- --                                                             603 100 20 0 -- --                                                             604 100 10 0 -- --                                                             605 100 20 .sup.    20(80) -- --                                               606   80.sup.d 20 0 -- --                                                      607  80 10 0 -- --                                                             608 100 30 0 -- --                                                             609 100 20 0 -- --                                                             610   0.sup.d 20 0 -- --                                                       611  30 30 0 -- --                                                             612    0(30).sup.a 20 0 -- --                                                  613    0(70).sup.a 50 0 -- --                                                  614  10 20 0 -- --                                                             615 100 20 0 -- --                                                             616 100  0 0 -- --                                                             617 100 10 0 -- --                                                             618 100 10 0 -- --                                                             619 100  0 0 -- --                                                             620  70 30 .sup.    20(40) -- --                                               621 100 10 0 -- --                                                             622 100 70 0 60(100) 100                                                       623 100  0 0 0 20(50)                                                          624 100 80 0 0 80(100)                                                         625 100 10 20  -- --                                                           626 100 90 0 -- --                                                             627 100  0 0 -- --                                                             628 100 40 0 -- --                                                             629 100  0 0 -- --                                                             630 100  0 0 -- --                                                             631 100  0 0 -- --                                                             632 100 30 0 -- --                                                             633 100 10 0 -- --                                                             634 100 90 0 -- --                                                             635   0.sup.d 100  0 0 0                                                       636   80.sup.d 100  0 0 0                                                      637 100 100  0 20(60) 100                                                      638 100 10 20  -- --                                                           639  10 20 0 -- --                                                             640 100 80 0 0 0                                                               641 100 30 0 -- --                                                             642 100 100  0 -- --                                                           643 100 20 0 -- --                                                             644 100 40 0 -- --                                                             645 100 20 0 -- --                                                             646 100  0 0 20 100                                                            647 100 60 20  20 40(60)                                                       648  70 100  0 80(20) 40(100)                                                  649 100 40 0 40 0(80)                                                          650  100.sup.c 10 0 0(40) 0(20)                                                651  90 60 40  80(60) 0(20)                                                    652  20 10 0 0(40) 40(60)                                                      653   0.sup.d  0 0 0(20) 0                                                     654  70 100  0 20(40) 0                                                        655  80 70 0 40(100) 40(80)                                                    656 100  0 0 0 100                                                             657  30  0 0 0 0                                                               658   40.sup.c 90 20  80(100) 0                                                659   30.sup.c 80 0 0(80) 0                                                    660   80.sup.c 70 0 0 0                                                        661 100 20 0 0 0                                                               662  70 40 20  0 0                                                             663 100  0 0 -- --                                                             664  100.sup.c  0 0 0 0                                                        665  60 30 .sup.    20(40) 0(20) 0                                             666 100  0 0 -- --                                                             667 100  0 0 -- --                                                             668   60.sup.d 20 0 -- --                                                      669   20.sup.d 30 0 -- --                                                      670  90 40 0 -- --                                                             671 100 30 0 -- --                                                             672 100 100  0 -- --                                                           673  20 40 0 -- --                                                             674 100 50 80  -- --                                                           675 100 30 0 -- --                                                             676  100.sup.c 80 0 -- --                                                      677   70.sup.c 40 0 -- --                                                      678  50 30 0 -- --                                                             679 100 30 0 -- --                                                             680 100 10 0 -- --                                                             681 100 100  0 -- --                                                           682  10 40 0 -- --                                                             683 100  0 0 0 20                                                              684   20.sup.a 100.sup.a   0 -- --                                             685   10.sup.c   10a,c 40  -- --                                               686   20.sup.c    0a,c 0 -- --                                                 687   0.sup.d   30a,c 0 -- --                                                  688 100 100  0 60(100) 100                                                     689  90 50 0 40(100) 0(20)                                                     690   0.sup.d  10.sup.d  0.sup.d 0.sup.d 0.sup.d                               691   30.sup.c 10 0 0 0                                                        692  80   0.sup.a 0 -- --                                                      693   0.sup.d 20 0 0 0                                                         694  80 80 40  0 0                                                             695   60.sup.d 30 0 0 0                                                        696   0.sup.d 40 20  20 0                                                      697   20.sup.c  0 0 0 0                                                        698 100  0 20  0 100                                                           699 100 100  0 60(100) 90                                                      700   0.sup.d   100a,c 0 0 0                                                   701   90.sup.c 10 20  40(20) 0                                                 702   0.sup.d 100  0 0 0                                                       703   10.sup.a   0.sup.a 0 -- --                                               704   0.sup.d 30 0 -- --                                                       705  80  0 0 -- --                                                             706  30 30 20  -- --                                                           707 100 40 0 -- --                                                             708 100 10 0 -- --                                                             709   80.sup.d 100  .sup.    20(40) -- --                                      710 100 30 0 -- --                                                             711 100 30 0 -- --                                                             712 100 20 0 -- --                                                             713 100 60 0 -- --                                                             714 100 40 0 -- --                                                             715 100 20 0 -- --                                                             716 100  0 0 -- --                                                             717 100 40 0 -- --                                                             718   10.sup.d 70 0 -- --                                                      719   0.sup.d 20 0 -- --                                                       720 100  0 0 -- --                                                             721 100 30 0 -- --                                                             722  50  0 40  0 0                                                             723 100 80 40  60(100) 90(100)                                                 724  90 10 0 0(20) 0                                                           725 100  0 0 0 0                                                               726 100 30 0 20 100                                                            727 100 30 0 100 100                                                           728   0.sup.d  20.sup.d  0.sup.d 0.sup.d                                       729 100 70 0 100 100                                                           730  70 50 0 40(20) 50(60)                                                     732 100  0 20  0 100                                                           733 100 50 0 0 80(100)                                                         734   10.sup.c  0 20  0 0                                                      735 100 10 0 20 80(100)                                                        736 100  0 0 0 90(100)                                                         737 100  0 0 0 0                                                               738 100 80 0 80 100                                                            739 100 20 0 0 0                                                               740  30 30 0 0 0                                                               741 100  0 0 -- 0                                                              742 100  0 0 -- 0                                                              743 100 40 0 -- 0                                                              744 100 20 0 -- 0                                                              745 100 10 0 -- 0                                                              746 100  0 0 -- 0                                                              747  70 20 0 -- 0                                                              748  100.sup.d 100.sup.d    0.sup.d 0.sup.d 0(10).sup.d                        749 100  0 0 -- 0                                                              750  20 30 0 -- 0                                                              751 100  0 20  -- 0                                                            752  10 20 0 -- 0                                                              753 100 20 0 -- 0                                                              754 100 70 0 -- 0                                                              755 100 10 0 -- 0                                                              756 100  0 0 -- --                                                             757 100  0 0 -- --                                                             758 100 100  0 -- --                                                           759 100 10 0 -- --                                                             760  100.sup.c 40 .sup.    20(40) -- --                                        761   0.sup.d 90 0 -- --                                                       762 100 40 0 -- --                                                             763 100 90 0 -- --                                                             764  80 80 0 0 50(90)                                                          765 100 10 0 40(100) 100                                                       766 100 20 20  0(20) 100                                                       767 100  0 0 0 0                                                               768  50 10 40  0 0                                                             769 100 20 20  0(20) 0                                                         770  50 30 20  0(20) 0                                                         771  50.sup.c  0 0 0(20) 0                                                     772  90 10 0 0(20) 0                                                           773  20 40 0 0 0                                                               774 100  0 20  20 90                                                           775 100 30 0 0 20(30)                                                          776  40  0 0 0 0                                                               777   60.sup.c   30a,c 20.sup.c  0 0                                           778 100 10 0 0 0                                                               779  90 20 0 0 0                                                               780 100  0 0 0 0                                                               781 100 80 0 40(100) 100                                                       782  40 70 0 0(20) 40                                                          783 100 10 0 0 10                                                              784 100 30 0 0 0                                                               785 100 20 0 40(0) 80(100)                                                     786  60  0 0 0 0                                                               787  30 30 0 -- --                                                             788  70 30 0 -- --                                                             789 100  0 0 -- --                                                             790 100 90 0 -- --                                                             791  20.sup.c 10 0 0 0                                                         792   0.sup.d   10a,c  0.sup.c 0 0                                             793  20  0 0 -- --                                                             794   0.sup.d 10 0 0 0                                                         795 100 30 0 -- --                                                             796 100 30 0 -- --                                                             797 100  0 0 -- --                                                             798 100 10 0 -- --                                                             799   0.sup.a   0.sup.a 0 0 0                                                  800   30.sup.a  30.sup.a 20 0 0                                                801   20.sup.c 10 0 0 0                                                        802 100 40 0 80 80(100)                                                        803 100 60 0 0 0                                                               804 100 30 0 0 0                                                               805 100 30 0 -- --                                                             806 100 20 0 -- --                                                             807 100  0 0 -- --                                                             808 100 20 0 -- --                                                             809 100  0 0 -- --                                                             810 100 50 0 -- --                                                             811  50  0 0 -- --                                                             812 100  0 60  -- --                                                           813 100  0 0 -- --                                                             814 100 20 20  -- --                                                           815 100  0 0 -- --                                                             816 100  0 0 -- --                                                             817 100 30 0 -- --                                                             818 100 40 0 -- --                                                             819  30 10 0 0(20) 0                                                           820 100   0.sup.a 0 0(20) 0                                                    821  100.sup.a 70 0 0(20) 0                                                    822  100.sup.a 100       40(100) 0(100) 100                                    823  100.sup.a   0.sup.a 0 -- --                                               824   0.sup.d 10 0 -- --                                                       825  100.sup.a 30 0 -- --                                                      826  100.sup.a   0.sup.a 0 -- --                                               827  60  10.sup.a 0 -- --                                                      828   0.sup.a   0.sup.a 20  -- --                                              829 100 100  0 20(80) 80(90)                                                   830  0 10 0 0 20                                                               831 100  0 0 0 0                                                               832 100  0 0 0 0                                                               833  60  0 0 0 20                                                              834  0  0 40  0 0                                                              835 100 90 0 60 100                                                            836  0 50 0 0 0                                                                837  0  0 20  0 0                                                              838  0 100  0 0 70                                                             839 100 40 0 0 100                                                             840  0  0 0 0 0                                                                841  0  0 20  0(20) 0                                                          842  10 20 0 0(20) 0                                                           843  40 50 0 20(60) 50(90)                                                     844  0 10 0 0 0                                                                845  70 10 0 0(40) 0                                                           846  40  0 40  20 0                                                            847  0 30 0 20 0                                                               848  40 30 20  0(60) 20(80)                                                    849  0 10 40  0 0                                                              850  10  0 0 0 0                                                               851  0  0 0 20 0                                                               852  0  0 0 20(40) 0                                                           853  0  0 0 0 0                                                                854  0 60 0 60 0                                                               855  0 90 0 0 0                                                                856 100  0 0 0 0                                                               857  50 20 20  0(20) 0                                                         858  0 10 0 0 0                                                                859  0 60 0 60 0                                                               860  0 10 0 0 0                                                                861  0 10 0 0 0                                                                862  0 10 0 0(40) 0                                                            863  0 20 0 0 0                                                                864  40  0 0 0 0                                                               865 100 50 0 0 0(20)                                                           866  0 100  0 0 0                                                              867  0 100  0 0 0                                                              868  10  0 20  0 0                                                             869  0  0 0 40 0                                                               870 100 10 0 0 80(90)                                                          871  0  0 0 0 0                                                                872  0 10 20  0 0                                                              873  0 20 0 -- --                                                              874 100  0 0 -- --                                                             875  20 20 0 -- --                                                             876 100 20 0 -- --                                                             877  80 10 0 -- --                                                             878 100 10 0 -- --                                                             879 100 10 0 -- --                                                             880 100 10 -- -- --                                                            881  80 80 40  0 0                                                             882 100  0 0 -- --                                                             883  90 50 0 0(20) 40(100)                                                     884  0  0 0 -- --                                                              885  90 30 0 -- --                                                             886 100 10 0 -- --                                                             887 100 100  0 -- --                                                           888  30 100  0 -- --                                                           889 100 40 0 -- --                                                             890 100 70 0 -- --                                                             891 100 20 0 -- --                                                             892 100 30 20  -- --                                                           893  0 40 0 -- --                                                              894 100  0 0 -- --                                                             895 100 20 0 -- --                                                             896 100 30 0 -- --                                                             897 100  0 0 -- --                                                             898 100 30 0 -- --                                                             899 100 10 0 -- --                                                             900 100  0 0 -- --                                                             901 100 10 0 -- --                                                             902 100  0 0 -- --                                                             903 100 30 0 -- --                                                             904 100  0 0 -- --                                                             905 100  0 0 -- --                                                             906  0 10 0 -- --                                                              907 100  0 0 -- --                                                             908 100 30 40  -- --                                                           909 100 30 0 -- --                                                             910 100 50 0 -- --                                                             911 100  0 0 -- --                                                             912 100 10 0 -- --                                                             913 100  0 0 -- --                                                             914  0  0 0 0 0                                                                915  90 10 0 0 0                                                               916  0  0 0 0 0                                                                917  0  0 20  0 0                                                              918  0  0 0 0 0                                                                919 100 40 20  0(20) 0                                                         920  0  0 0 0 0                                                                921  0 90 20  20 0                                                             922  0  0      0(40) 0 0                                                       923  0 30 0 -- --                                                              924   0.sup.a  10.sup.a 0 -- --                                                925 -- -- -- -- --                                                             926  0 100  20  0 60(100)                                                      927  0  0 0 0 20                                                               928  20 30 0 0 20                                                              929  0 60 0 0 0(20)                                                            930  0 80 0 0 0                                                                931  0 100  0 20(20) 20                                                        932 100 40 0 40 0(20)                                                          933  0  0 -- -- --                                                             934 100 100  0 20 0                                                            935  0  0 0 -- --                                                              936  0 40 0 0 40                                                               937  0 10 0 0 40                                                               938  0  0 0 0 20                                                               939  0  0 0 0 0                                                                940  10 10 -- -- --                                                            941  0 10 -- -- --                                                             942  0  0 -- -- --                                                             943  0  0 0 -- --                                                              944  0  0 -- -- --                                                             945  0  0 0 0 0                                                                946  0 20 -- -- --                                                             947  0 20 0 -- --                                                              948  0 20 -- -- --                                                             949  0 10 0 0 20                                                               950  0  0 0 0 0                                                                951  0  0 0 0 20(40)                                                           952  0 20 0 0 0                                                                953  0  0 0 -- --                                                              954  0  0 20  0 0                                                              955  0  0 20  0 20(40)                                                         956  40 10      0(20) 0 0                                                      957  40 60 0 0 0                                                               958  0  0 0 0 0                                                                959  0  0 0 0 20                                                               960  0  0 0 0 0                                                                961  0 100  40  0(20) 0                                                        962 -- -- -- -- --                                                             963  0 50 0 20 0                                                               964  20 100  0 20 0                                                            965  0 60 60  20(40) 0                                                         966   0.sup.a   0.sup.a 0 -- --                                                967   0.sup.a   0.sup.a 0 -- --                                                968  0 30 0 0 20                                                               969  0 -- -- -- --                                                             970  0 -- -- -- --                                                             971  0 -- -- -- --                                                             972  0 -- -- -- --                                                             973  0 -- -- -- --                                                             974  0 -- -- -- --                                                             975  0 -- -- -- --                                                             976  10 -- -- -- --                                                            977  0 -- -- -- --                                                             978  60 -- -- -- --                                                            979   100(80) .sup.    0(20) 0 -- --                                           980 100 .sup.    0(30) 0 -- --                                                 981 100  0 0 -- --                                                             982 100      10(40) 0 -- --                                                    983    0(30)      10(20) 0 -- --                                               984  30 10 0 -- --                                                             985  0 20 0 -- --                                                              986  0  0 0 -- --                                                              987  0  0 0 -- --                                                              988  0  0 0 -- --                                                              989  0  0 0 -- --                                                              990  0 30 0 -- --                                                              991  0  0 0 -- --                                                              992  0  0 0 -- --                                                              993  0  0 0 -- --                                                              994  0  0 0 -- --                                                              995  0  0 0 -- --                                                              996  20 20 0 -- --                                                             997  0 30 0 -- --                                                              998  0  0 0 -- --                                                              999  0  0 0 -- --                                                              1000   0  0 0 -- --                                                            1001   0 10 0 -- --                                                            1002   0  0 20  -- --                                                          1003   0 10 0 -- --                                                            1004   0  0 0 -- --                                                            1005   0 -- -- -- --                                                           1006   0 -- -- -- --                                                           1007  100  0 0 -- --                                                           1008   0 20 0 -- --                                                            1009   0 30 0 -- --                                                            1010   0 20 0 -- --                                                            1011   0  0 0 -- --                                                            1012   0  0 0 -- --                                                            1013   0 40 0 -- --                                                            1014   0  0 20  -- --                                                          1015   0 10 0 -- --                                                            1016  100  0 0 -- --                                                           1017  100 40 0 -- --                                                           1018   10  0 20  -- --                                                       ______________________________________                                    

Not all compounds were tested by soil application. The results of the compounds tested are reported.

It should be understood that the instant specification and examples are set forth by way of illustration and not limitation, and that various modifications and changes may be made without departing from the spirit and scope of the present invention as defined by the appended claims. 

We claim:
 1. A compound of the formula ##STR48## wherein X and X' are independently selected from O, S and NR, wherein R is selected from hydrogen and (C₁ -C₆)alkyl;E is selected from;1) an unsubstituted tertiary-carbon containing (C₄ -C₁₀) alkyl or substituted tertiary-carbon containing (C₃ -C₁₀) alkyl wherein the substituents are independently selected from 1 to 4 alkenyl, cyano, cycloalkyl, halogen, and phenyl and wherein the sum of non-hydrogen atoms in E is from 4 to 14, E does not have a chain length of non-hydrogen atoms greater than 5, and E does not contain more than one cyano group; and 2) an unsubstituted or substituted non-tertiary-carbon containing (C₄ -C₁₀) alkyl wherein the substituents are independently selected from 1 to 4 alkenyl, cyano, cycloalkyl, halogen, phenyl, and trimethylsilyl and wherein the sum of non-hydrogen atoms in E is from 5 to 14, E does not have a chain length of non-hydrogen atoms greater than 5, and E does not contain more than one cyano group; A and B are independently selected from;1) unsubstituted or substituted naphthyl wherein the substituents are independently selected from 1 to 3 halo; nitro; (C₁ -C₄)alkoxy; (C₁ -C₄)alkyl; and amino; 2) unsubstituted or substituted phenyl wherein the substituents are independently selected from 1 to 5 halo; nitro; cyano; hydroxy; (C₁ -C₆)alkyl; (C₁ -C₆)haloalkyl; (C₁ -C₆)cyanoalkyl; (C₁ -C₆)hydroxyalkyl; (C₁ -C₆)alkoxy; (C₁ -C₆)haloalkoxy; (C₁ -C₆)alkoxy(C₁ -C₆)alkyl; (C₁ -C₆)alkoxy(C₁ -C₆)alkoxy; (C₁ -C₆)alkylthio(C₁ -C₆)alkoxy; (C₁ -C₆)alkanoyloxy(C₁ -C₆)alkyl; (C₂ -C₆)alkenyl optionally substituted with halo, cyano, (C₁ -C₄)alkyl, or (C₁ -C₄)alkoxy; (C₂ -C₆)alkenyloxy; (C₂ -C₆)alkenylcarbonyl; (C₂ -C₆)alkenyloxycarbonyloxy; (C₂ -C₆)alkynyl optionally substituted with halo or (C₁ -C₄)alkyl; carboxy; (C₁ -C₆)alkylcarboxy(C₁ -C₆)alkyl); (C₁ -C₆)alkylcarbonyl; (C₁ -C₆)haloalkylcarbonyl; (C₁ -C₆)alkoxycarbonyl; (C₁ -C₆)haloalkoxycarbonyl; (C₁ -C₆)alkanoyloxy (--OCOR); (C₁ -C₆)alkoxycarbonyl(C₁ -C₆)alkoxy; amino (--NRR'); carboxamido (--CONRR'); (C₂ -C₆)alkenylcarbonylamino; (C₁ -C₆)hydroxyalkylaminocarbonyl; aminocarbonyloxy (--OCONRR'); amido (--NRCOR'); alkoxycarbonylamino (--NRCO₂ R'); thiocyanato; isothiocyanato; (C₁ -C₆)thiocyanatoalkyl; (C₁ -C₆)alkylthio; sulfoxide (--S(O)R); sulfonyl (--SO₂ R); alkylsulfonyloxy (--OSO₂ R); sulfonamide (--SO₂ NRR'); alkylthiocarbonyl (--CSR); thioamido (--NRCSR'); unsubstituted or substituted phenyl wherein the substituents are independently selected from 1 to 3 halo, cyano, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)haloalkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino, and (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; unsubstituted or substituted phenoxy wherein the substituents are independently selected from 1 to 3 halo, cyano, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)haloalkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino, and (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; unsubstituted or substituted benzoyl wherein the substituents are independently selected from 1 to 3 halo, cyano, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)haloalkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino and (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; benzoyloxy(C₁ -C₆)alkyl; phenylthio(C₁ -C₆)alkyl wherein the phenyl ring is unsubstituted or substituted with 1 to 3 substituents independently selected from halo, cyano, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)haloalkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino, and (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; imino (--CR═N--R²) wherein R² is selected from hydroxy, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, amino (--NRR'), phenylamino, carbonyl (--COR), and benzoyl; acetylthiosemicarbazone; or when two adjacent positions on the phenyl ring are substituted with alkoxy groups, these groups, together with the carbon atoms to which they are attached, may be joined to form a 5 or 6 membered dioxolano or dioxano heterocyclic ring; and 3) unsubstituted or substituted five-membered heterocycle selected from furyl, thienyl, triazolyl, pyrrolyl, isopyrrolyl, pyrazolyl, isoimidazolyl, thiazolyl, isothiazolyl, oxazolyl, and isooxazolyl wherein the substituents are independently selected from 1 to 3 halo; nitro; hydroxy; (C₁ -C₆)alkyl; (C₁ -C₆)alkoxy; carboxy; (C₁ -C₆)alkoxycarbonyl (--CO₂ R); (C₁ -C₆)alkylcarboxy(C₁ -C₆)alkyl (--RCO₂ R'); carboxamido (--CONRR'); amino (--NRR'); amido (--NRCOR'); (C₁ -C₆)alkylthio; or unsubstituted or substituted phenyl wherein the substituents are independently selected from one to three halo, nitro, (C₁ -C₆)alkyl, (C₁ -C₆)haloalkyl; (C₁ -C₆)alkoxy; (C₁ -C₆)haloalkoxy; carboxy, (C₁ -C₄)alkoxycarbonyl (--CO₂ R); or amino (--NRR'); wherein R, R' and R" are selected from hydrogen and (C₁ -C₆)alkyl;and agronomically acceptable salts thereof; provided that:1) when X and X' are O and A and B are unsubstituted phenyl, then E is other than 2-methylpropyl (--CH₂ CH(CH₃)₂); 3-methylbutyl (--CH₂ CH₂ CH(CH₃)₂); neopentyl (2,2-dimethylpropyl; --CH₂ C(CH₃)₃) or cyclohexylmethyl (--CH₂ C₆ H₁₁); or 2) when X and X' are O, and A is unsubstituted phenyl or phenyl substituted with 1 to 2 substituents independently selected from (C₁ -C₆)alkyl and halo, and B is unsubstituted phenyl or phenyl substituted with 1 to 2 substituents independently selected from halo, nitro, and (C₁ -C₆)alkyl, then E is other than halo(C₂ -C₆)alkyl; or 3) when X and X' are O, and E is t-butyl (--C(CH₃)₃), and A is unsubstituted phenyl, then B is other than 4-nitrophenyl; or 4) when one of A and B is an unsubstituted or substituted five-membered heterocycle then the other of A and B is other than an unsubstituted or substituted five-membered heterocycle; or 5) when A is phenyl substituted with from two to three substituents in the 2, 3, and 4 positions wherein the 3 substituent is (C₁ -C₆)alkoxy, the 2 substituent is selected from halo and (C₁ -C₆)alkyl, and, when substituted, the 4 substituent is (C₁ -C₆)alkyl then B is other than unsubstituted phenyl or phenyl substituted with from one to four substituents in the 2, 3, 4, and 5 positions wherein the 2 substituent is selected from halo, and (C₁ -C₆)alkyl and the 3, 4, and 5 substituents are independently selected from bromo, chloro, fluoro, and (C₁ -C₆)alkyl.
 2. The compound of claim 1 whereinX and X' are independently selected from O and S; E is selected from(1) an unsubstituted or substituted tertiary-carbon containing (C₃ -C₁₀) alkyl wherein the substituents are independently selected from 1 to 4 alkenyl, cyano, cycloalkyl, halogen, and phenyl and wherein the sum of non-hydrogen atoms in E is from 4 to 14, E does not have a chain length of non-hydrogen atoms greater than 5, and E does not contain more than one cyano group; and (2) an unsubstituted or substituted non-tertiary-carbon containing (C₄ -C₁₀) alkyl wherein the substituents are independently selected from 1 to 4 alkenyl, cyano, cycloalkyl, halogen, phenyl, and trimethylsilyl and wherein the sum of non-hydrogen atoms in E is from 5 to 14; and A and B are independently selected from(1) unsubstituted or substituted naphthyl wherein the substituents are independently selected from 1 to 3 halo; nitro; (C₁ -C₄)alkoxy; (C₁ -C₄)alkyl; and amino; and (2) unsubstituted or substituted phenyl wherein the substituents are independently selected from 1 to 5 halo; nitro; cyano; hydroxy; (C₁ -C₆)alkyl; (C₁ -C₆)haloalkyl; (C₁ -C₆)cyanoalkyl; (C₁ -C₆)hydroxyalkyl; (C₁ -C₆)alkoxy; (C₁ -C₆)haloalkoxy; (C₁ -C₆)alkoxy(C₁ -C₆)alkyl; (C₁ -C₆)alkoxy(C₁ -C₆)alkoxy; (C₁ -C₆)alkylthio(C₁ -C₆)alkoxy; (C₁ -C₆)alkanoyloxy(C₁ -C₆)alkyl; (C₂ -C₆)alkenyl optionally substituted with halo, cyano, (C₁ -C₄)alkyl, or (C₁ -C₄)alkoxy; (C₂ -C₆)alkenyloxy; (C₂ -C₆)alkenylcarbonyl; (C₂ -C₆)alkenyloxycarbonyloxy; (C₂ -C₆)alkynyl optionally substituted with halo or (C₁ -C₄)alkyl; carboxy; (C₁ -C₆)alkylcarboxy(C₁ -C₆)alkyl); (C₁ -C₆)alkylcarbonyl; (C₁ -C₆)haloalkylcarbonyl; (C₁ -C₆)alkoxycarbonyl; (C₁ -C₆)haloalkoxycarbonyl; (C₁ -C₆)alkanoyloxy (--OCOR); (C₁ -C₆)alkoxycarbonyl(C₁ -C₆)alkoxy; amino (--NRR'); carboxamido (--CONRR'); (C₂ -C₆)alkenylcarbonylamino; (C₁ -C₆)hydroxyalkylaminocarbonyl; aminocarbonyloxy (--OCONRR'); amido (--NRCOR'); alkoxycarbonylamino (--NRCO₂ R'); thiocyanato; isothiocyanato; (C₁ -C₆)thiocyanatoalkyl; (C₁ -C₆)alkylthio; sulfoxide (--S(O)R); sulfonyl (--SO₂ R); alkylsulfonyloxy (--OSO₂ R); sulfonamide (--SO₂ NRR'); alkylthiocarbonyl (--CSR); thioamido (--NRCSR'); unsubstituted or substituted phenyl wherein the substituents are independently selected from 1 to 3 halo, cyano, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)haloalkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino, and (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; unsubstituted or substituted phenoxy wherein the substituents are independently selected from 1 to 3 halo, cyano, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)haloalkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino, and (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; unsubstituted or substituted benzoyl wherein the substituents are independently selected from 1 to 3 halo, cyano, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)haloalkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino and (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; benzoyloxy(C₁ -C₆)alkyl; phenylthio(C₁ -C₆)alkyl wherein the phenyl ring is unsubstituted or substituted with 1 to 3 substituents independently selected from halo, cyano, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)haloalkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ C-₄)alkylamino, and (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; imino (--CR═N--R²) wherein R² is selected from hydroxy, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, amino (--NRR'), phenylamino, carbonyl (--COR), and benzoyl; acetylthiosemicarbazone; or when two adjacent positions on the phenyl ring are substituted with alkoxy groups, these groups, together with the carbon atoms to which they are attached, may be joined to form a 5 or 6 membered dioxolano or dioxano heterocyclic ring; or agronomically acceptable salts thereof.
 3. The compound of claim 1 whereinX and X' are O or S; E is branched (C₃ -C₈)alkyl; and A and B are the same or different unsubstituted naphthyl or unsubstituted or substituted phenyl wherein the substituents are independently selected from 1 to 5 halo; nitro; cyano; (C₁ -C₄)alkyl; (C₁ -C₄)haloalkyl; (C₁ -C₄)cyanoalkyl; (C₁ -C₄)alkoxy; (C₁ -C₄)alkoxyalkyl having independently the stated number of carbon atoms in each alkyl group; carbonyl (--COR); (C₁ -C₄)alkoxycarbonyl; (C₁ -C₄)alkanoyloxy; thiocyanato; unsubstituted or substituted phenyl having one or two of the same or different halo, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino or (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group; or phenoxy where the phenyl ring is unsubstituted or substituted with one or two of the same or different halo, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, carboxy, amino, (C₁ -C₄)alkylamino or (C₁ -C₄)dialkylamino having independently the stated number of carbon atoms in each alkyl group where R is hydrogen or (C₁ -C₄)alkyl; or agronomically acceptable salts thereof.
 4. The compound of claim 1 whereinX and X' are O; E is branched (C₄ -C₇)alkyl; and A and B are independently selected from unsubstituted or substituted phenyl wherein the substituents are independently selected from 1 to 3 halo, nitro, (C₁ -C₄)alkyl, (C₁ -C₄)alkoxy, or (C₁ -C₄)haloalkyl; or agronomically acceptable salts thereof.
 5. The compound of claim 1 whereinX and X' are O; E is selected from tertiary butyl, neopentyl (2,2-dimethylpropyl), and 1,2,2-trimethylpropyl; and A and B are independently selected from unsubstituted phenyl or substituted phenyl wherein the substituents are independently selected from 1 to 3 chloro, fluoro, bromo, iodo, nitro, methyl, ethyl, methoxy, and trifluoromethyl; or agronomically acceptable salts thereof.
 6. The compound of claim 3 whereinA is a substituted phenyl wherein the substituents are selected from 1 substituent in the 4-position and 1 substituent in each of the 2 and 3-positions; and B is phenyl substituted with from 1 to 3 substituents.
 7. The compound of claim 3 whereinA is a substituted phenyl wherein the substituents are selected from 1 substituent in the 4-position and 1 substituent in each of the 2 and 3-positions; and B is phenyl substituted with 1 substituent in each of the 3 and 5-positions.
 8. A compound of the formula ##STR49## wherein R^(a) is selected from hydrogen, halo and (C₁ -C₆)alkyl;R^(b) is selected from hydrogen, unsubstituted (C₁ -C₆)alkoxy, and halo substituted (C₁ -C₆)alkoxy; R^(c) is selected from hydrogen, halo, (C₁ -C₆)alkyl, (C₁ -C₆)alkoxy, (C₁ -C₆)alkoxy(C₁ -C₆)alkyl, and nitro; R^(d), R^(e), and R^(f) are independently selected from hydrogen, bromo, chloro, fluoro, (C₁ -C₆)alkyl, (C₁ -C₆)alkoxy, and (C₁ -C₆)alkoxy(C₁ -C₆)alkyl; R^(g) is a branched (C₄ -C₆)alkyl; and R^(h) is selected from hydrogen, (C₁ -C₆)alkoxy, (C₁ -C₆)alkyl, and, when taken together with R^(b), methylenedioxy, 1,2-ethylenedioxy, 1,2-ethyleneoxy, and 1,3-propyleneoxy wherein an oxo atom is located at the R^(b) position; and the substituent pairs selected from R^(c) and R^(d), and R^(d) and R^(e), and R^(e) and R^(f) when taken together can be methylenedioxy or 1,2-ethylenedioxy; provided that;one of R^(a) and R^(b) and R^(h) must be other than hydrogen and one of R^(c) and R^(d) and R^(e) and R^(f) must be other than hydrogen; and when R^(b) is (C₁ -C₆)alkoxy, and R^(a) is selected from halo and (C₁ -C₆)alkyl, and R^(h) is selected from hydrogen and (C₁ -C₆)alkyl then the phenyl ring substituted with R^(c), R^(d), R^(e), and R^(f) is other than substituted phenyl wherein R^(c) is selected from hydrogen, halo, and (C₁ -C₆ alkyl and R^(d), R^(e), and R^(f) are independently selected from hydrogen, bromo, chloro, fluoro, and (C₁ -C₆)alkyl; and agronomically acceptable salts thereof.
 9. The compound of claim 8 whereinR^(a) and R^(b) are other than hydrogen and R^(h) is hydrogen or R^(h) is other than hydrogen and R^(a) and R^(b) are hydrogen.
 10. The compound of claim 8 whereinR^(c) and R^(e) are hydrogen; and R^(d) and R^(f) are other than hydrogen.
 11. The compound of claim 8 whereinR^(a) and R^(b) are other than hydrogen and R^(h) is hydrogen or R^(h) is other than hydrogen and R^(a) and R^(b) are hydrogen; R^(c) and R^(e) are hydrogen; and R^(d) and R^(f) are other than hydrogen.
 12. The compound of claim 8 whereinR^(a) and R^(b) are hydrogen, R^(c) is hydrogen, R^(d) is methyl, R^(e) is hydrogen, R^(f) is methyl, R^(g) is t-butyl, and R^(h) is ethyl; or R^(a), R^(b), R^(c), R^(d), R^(e), and R^(f) are hydrogen, R^(g) is t-butyl, and R^(h) is chloro. 